Synthesis of glycine

Preparation of glycine

Preparation of glycine from chloroacetic acid and ammonium carbonate

Preparation of glycine from chloroacetic acid and ammonium carbonate

Preparation of glycine from chloroacetic acid and ammonium carbonate

8 moles of ammonium carbonate in 140 ml of water is heated to 55 °C in a round-bottomed flask with a reflux condenser, cooled to 40°C with shaking, and treated at this temperature with 6 moles of concentrated ammonia. This mixture is then allowed to stand for 30 min. Then 1 mole of the alpha-halogenocarboxylic acid is added gradually, and the mixture is left at 40-50°C for 24 hours if bromoacetic acid and for 40 hours if chloroacetic is used. Then ammonia and carbon dioxide are driven off by heating the product in a porcelain dish over a free flame, and the solution is concentrated until the internal temperature has reached 110°C. The solution is cooled to 60°C and treated with 3 litres of methanol. After standing overnight in the refrigerator, the solid matter is filtered off and is washed with methanol. The yield of glycine is 70%, m.p. 232 °C.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 214, (1973)

Preparation of glycine from chloroacetic acid and ammonia

Preparation of glycine from chloroacetic acid and ammonia

Preparation of glycine from chloroacetic acid and ammonia

600 ml of ammonium hydroxide (d=0.907) is added into a wide-necked flask and from a dropping funnel a solution of 50 g of chloroacetic acid dissolved in 50 ml of water is added dropwise. During the addition the reaction mixture is constantly stirred. When the addition of chloroacetic acid is complete, the obtained solution is allowed to cool to room temperature and kept overnight. The next day reaction mixture is heated in order to remove an excess of ammonia. When the ammonia has disappeared copper carbonate is added in powder form to the hot liquid until effervescence ceases. The obtained blue solution is filter and evaporated until crystals of copper glycinate begin to separate. The cooled solution is filtered yielding the blue needles of copper glycinate. Additional portion of copper glycinate is obtained by evaporating the mother liquid. to obtain glycine, copper glycinate is dissolve in water and hot solution is saturated with a current of hydrogen sulfide. Finally the solution is filtered in order to remove copper sulfide and evaporated to a small bulk yielding colorless crystals of glycine, which are dried in a vacuum desiccator.

A class-book of organic chemistry, by J. B. Cohen, 231-232, 1918

Preparation of glycine from potassium phthalimide and chloroacetic ethyl ester

 

Preparation of glycine from potassium phthalimide and chloroacetic ethyl ester

Preparation of glycine from potassium phthalimide and chloroacetic ethyl ester

A mixture of 10 g of potassium phthalimide and 6.5 g of chloroacetic ester is heated together with proper stirring in the oil-bath at 150° C with reflux condenser. After 30 min the mass becomes pasty, and on cooling is dissolved in hot 50% ethyl alcohol. The product is filtered, when cold, and wash first with cold 50%, alcohol and then with water to remove potassium chloride yielding 6-8 g of 2-phthalimidoethyl acetate (ethyl (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetate). After crystallization from dilute alcohol, 2-phthalimidoethyl acetate melts at 112-113° C. In order to hydrolyse the phthalyl glycine ester, 2-5 g are boiled with reflux for a short time with 1-2 g of potassium hydroxide in 12 ml of water. The ester passes into solution which is treated, when cold, with 2.2 ml of conc. hydrochloric acid. On standing a short time, colorless crystals of N-phthaloylglycine separate which are filtered and washed with ice-cold water until the filtrate no longer gives the reaction for chloride ion. A double the weight of 20% hydrochloric acid is added and the reaction mixture is boiled under reflux with occasional stirring until a clear solution is obtained. The phthalic acid separates after two hours then the solution is filtered, filtrate is evaporated, the glycine, which remains, is washed with a little alcohol and dried.

A Class-Book of Organic Chemistry, by J. B. Cohen, 54, 1919

 

IUPAC Name

2-aminoacetic acid

InChI

InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)

InChI Key

DHMQDGOQFOQNFH-UHFFFAOYSA-N

Canonical SMILES

C(C(=O)O)N

MeSH Synonyms

Acid, Aminoacetic, Aminoacetic Acid, Calcium Salt Glycine, Cobalt Salt Glycine, Copper Salt Glycine, Glycine, Glycine Carbonate (1:1), Monosodium Salt, Glycine Carbonate (2:1), Monolithium Salt, Glycine Carbonate (2:1), Monopotassium Salt, Glycine Carbonate (2:1), Monosodium Salt, Glycine Hydrochloride, Glycine Hydrochloride (2:1), Glycine Phosphate, Glycine Phosphate (1:1), Glycine Sulfate (3:1), Glycine, Calcium Salt, Glycine, Calcium Salt (2:1), Glycine, Cobalt Salt, Glycine, Copper Salt, Glycine, Monoammonium Salt, Glycine, Monopotasssium Salt, Glycine, Monosodium Salt, Glycine, Sodium Hydrogen Carbonate, Hydrochloride, Glycine, Monoammonium Salt Glycine, Monopotasssium Salt Glycine, Monosodium Salt Glycine, Phosphate, Glycine, Salt Glycine, Monoammonium, Salt Glycine, Monosodium

Depositor-Supplied Synonyms

glycine, aminoacetic acid, 2-Aminoacetic acid, Glycocoll, Aminoethanoic acid, Glycolixir, 56-40-6, Glicoamin, Glycosthene, Aciport, Padil, Hampshire glycine, Amitone, Acetic acid, amino-, Leimzucker, Gyn-hydralin, Aminoazijnzuur, Glycine, non-medical, L-Glycine, Sucre de gelatine, Corilin, H-Gly-OH, GLY (IUPAC abbrev), polyglycine, (1-13c)glycinato, Glycinum [INN-Latin], Glicina [INN-Spanish], Glycine [INN], (15N)Glycine, FEMA No. 3287, CCRIS 5915, Glicina, Glycinum, Glykokoll, HSDB 495, Glyzin, Aminoessigsaeure, gly, Hgly, Polyglycine II, Acide aminoacetique [INN-French], Acido aminoacetico [INN-Spanish], Acidum aminoaceticum [INN-Latin], AI3-04085, Acido aminoacetico, Acide aminoacetique, UNII-TE7660XO1C, NSC 25936, Acidum aminoaceticum, L-alpha-amino acids, 2,2-dialkylglycines, CHEBI:15428, Tocris-0219, GLYCINE, ACS, NSC25936, EINECS 200-272-2, Biomol-NT_000195, bmse000089, CHEMBL773, H2N-CH2-COOH, WLN: Z1VQ, AC1L19XW, AC1Q28JW, Glycine, homopolymer (VAN), NCGC00024503-01, G5417_SIGMA, G5523_SIGMA, G7126_SIGMA, G7403_SIGMA, G8790_SIGMA, G8898_SIGMA, P8791_SIGMA, GLYCINE 1.5% IN PLASTIC CONTAINER, Glycine-UL-14C hydrochloride, W328707_ALDRICH, Glycine iron sulphate (1:1), 15527_RIEDEL, 33226_RIEDEL, AC1Q53O0, BPBio1_001222, 50046_FLUKA, 50046_SIGMA, 6000-43-7 (hydrochloride), CHEBI:15705, CHEBI:16228, 2-aminoaceticacid, Glycine, labeled with carbon-14, DHMQDGOQFOQNFH-UHFFFAOYSA-N, 15527_SIAL, 33226_SIAL, KST-1A2919, KST-1A8102, 17829-66-2 (cobalt salt), 32817-15-5 (copper salt), aminoacetate, 33242-26-1 (calcium salt), AB-131/40217813, 410225_SIAL, AMINOACETIC ACID 1.5% IN PLASTIC CONTAINER, Athenon, 29728-27-6 (monoammonium salt), AR-1A0345, AR-1A0532, LS-218, AKOS000119626, 15743-44-9 (mono-potassium salt), DB00145, 513-29-1 (sulfate (3:1)), 6000-44-8 (mono-hydrochloride salt), 7490-95-1 (hydrochloride (2:1), NCGC00024503-02, 7490-95-1 (hydrochloride (2:1)), 71295-98-2 (phosphate (1:1)), AB1002628, DSSTox_CID_667, Glycine, free base, 35947-07-0 (calcium salt (2:1)), FT-0083159, G0099, G0317, C00037, D00011, DSSTox_RID_75720, 63183-41-5 (hydrochloride hydrogen carbonate), DSSTox_GSID_20667, L001246, 25718-94-9, S04-0135, an alpha amino acid ester, B72BA06C-60E9-4A83-A24A-A2D7F465BB65, InChI=1/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5, CAS-56-40-6, 18875-39-3, 52955-63-2, 57678-19-0, 848646-45-7, 87867-94-5, Aminoethanoate, N-alkylglycines, amino-Acetate, CID750, amino-Acetic acid, [3H]glycine, [14C]glycine, 2-aminoethanoic acid, nchem.554-comp2, [14C]-glycine, Corilin (Salt/Mix), 112898-03-0, nchembio.121-comp9, nchembio.265-comp9, alpha-amino acid esters, PubChem18924, nchembio.145-comp33, nchembio.198-comp12, nchembio.266-comp30, NH2CH2COOH, Glycine (JP15/USP), Glycine (JP16/USP), bmse000977, GTPL727, KSC205S9D, NChemBio.2007.13-comp1, GTPL4084, GTPL4635, TE7660XO1C, CHEBI:46874, CHEBI:66933, CTK1A5991, HMDB00123, MolPort-000-871-607, Pharmakon1600-01300021, CPD-8569, Tox21_113575, ANW-32505, DAP000288, NSC-25936, NSC760120, Tox21_113575_1, AM81781, MCULE-2415764032, NSC-760120, RP08772, RTC-066530, NCGC00024503-03, AJ-51834, AK-77854, AN-24439, BC204500, BP-31024, BR-77854, KB-52268, DB-029870, ST2416448, TC-066530, FT-0600491, A20662, Aminoacetic acid; Aminoethanoic acid; Glycocoll, M-6155, M03001, Tris-tricine buffer; Tris-glycine buffer;Tris glycine buffer concentrate

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