Synthesis of carbohydrazide

Preparation of carbohydrazide

Preparation of carbohydrazide

Preparation of carbohydrazide

Three hundred fifty-four grams of diethyl carbonate (3.0 mols) and 388 g of 85% hydrazine hydrate (6.6 mols) are placed in a 1-liter round-bottomed flask equipped with a thermometer. The reactants are only partially miscible at the beginning of the reaction; the flask is shaken until a single phase is formed. This process is accompanied by the evolution of heat, causing the temperature to rise to about 55° C. The flask is then connected, to a fractionating column filled with Raschig rings to a depth of about 22 cm. A still head, fitted with a thermometer and a water-cooled condenser, is attached to the fractionating column. A Glas-col heater regulated by a variable transformer is employed to heat the reaction mixture. Distillation of the alcohol and water is quite rapid (5 ml/min.) for the first 30 minutes but decreases as the reaction proceeds. Heating is continued for 4 hours, during which time 325 to 350 ml of distillate is collected at a vapor temperature of 80 to 85° C; the pot temperature rises from 96 to 119° C. The pot liquor is cooled to 20° C and allowed to stand for at least 1 hour. Crystals of carbohydrazide separate and are filtered and dried as completely as possible by suction. The crude product weighs approximately 165 g.(60% yield). If necessary, purification may be effected by recrystallization from water. The product is dissolved in 110 ml of hot water, and the solution is filtered free of insoluble material. Precipitation is then effected by adding approxi­mately 500 ml of 95% ethanol. After standing for at least 1 hour at 20° C, the precipitate is filtered and washed with ether. The pure carbohydrazide weighs about 133 g., representing a recovery of 80 % of the crude material and a 49% overall yield based on the amount of diethyl carbon­ate employed.

Inorganic Syntheses, Vol. 4, 32-35, 1953

IUPAC Name

1,3-diaminourea

InChI

InChI=1S/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6)

InChI Key

XEVRDFDBXJMZFG-UHFFFAOYSA-N

Canonical SMILES

C(=O)(NN)NN

MeSH Synonyms

carbohydrazide

Depositor-Supplied Synonyms

Carbohydrazide, 1,3-Diaminourea, Carbonic dihydrazide, Carbazide, Carbonohydrazide, 497-18-7, Carbodihydrazide, Hydrazine, carbonyldi-, Hydrazine, carbonylbis-, Carbazic acid, hydrazide, Semicarbazide, 4-amino-, Carbonic acid, dihydrazide, Hydrazinecarboxamide, N-amino-, Cabazide, Karbazid, Urea, 1,3-diamino-, Urea, N,N’-diamino-, Hydrazinecarboxylic acid, hydrazide, Karbazid [Czech], 1,3-Diaminomocovina, NSC 1934, UNII-W8V7FYY4WH, 1,3-Diaminomocovina [Czech], XEVRDFDBXJMZFG-UHFFFAOYSA-N, EINECS 207-837-2, BRN 1747069, AI3-52397, diaminourea, Carbonohydrazid, carbonodihydrazide, N,N’-diaminourea, Urea,3-diamino-, Urea,N’-diamino-, 4-aminosemicarbazide, carbonylbis-hydrazine, hydrazinecarbohydrazide, 1,3-bis(azanyl)urea, ACMC-1AEZI, WLN: ZMVMZ, AC1Q5PXL, N-aminohydrazinecarboxamide, W8V7FYY4WH, N-aminohydrazine carboxamide, AC1L2KV4, C11006_ALDRICH, KSC235S0J, CHEBI:61308, CTK1D5904, hydrazide hydrazinecarboxylic acid, NSC1934, MolPort-001-764-626, NSC-1934, ANW-30830, AKOS003193931, RL03822, AN-21408, H247, KB-48688, LS-51887, DB-029568, RT-000598, 35941P, 4-03-00-00240 (Beilstein Handbook Reference), A827826, I06-0392, 3B3-012211

Removed Synonyms

HYDRAZINECARBOXAMIDE, CID73948, c0803, C019289

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