Synthesis of saccharin

Preparation of saccharin

Preparation of saccharin

Preparation of saccharin

One equivalent of the o-toluenesulfonamide is dissolved one equivalent of sodium hydroxide (40 g) and 2500  ml of water. This is heated to 40-50° C, and 256 g of solid potassium permanganate are slowly added with stirring. When all the potassium permanganate has been added and the colour has almost disappeared, a little sodium hydrosulfide is added to decolourise it completely, and the precipitated manganese compound is filtered off and washed with water until acid added to the filtrate gives no precipitate of saccharin. The combined filtrate and washings are then cooled down to ordinary temperature and neutralised with hydrochloric acid, using methyl orange as indicator. This treatment precipitates changed o-toluenesulfonamide, which is filtered off. Hydrochloric acid is then added to the filtrate, and the precipitated saccharin filtered off, washed with water, and dried at 40° C yielding white crystalline powder; m.p. 220° C; soluble in hot water and in alcohol, and in alkalis or alkali carbonates with the formation of salts. About 500 times sweeter than cane sugar.

Systematic organic chemistry, by W. M. Cumming, 318, 1937.

IUPAC Name

1,1-dioxo-1,2-benzothiazol-3-one

InChI

InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)

InChI Key

CVHZOJJKTDOEJC-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(=O)NS2(=O)=O

MeSH Synonyms

Calcium, Saccharin, Saccharin, Saccharin Calcium, Saccharin Sodium

Depositor-Supplied Synonyms

saccharin, Saccharine, o-Benzoic sulfimide, o-Sulfobenzimide, Saccharimide, Benzosulfimide, 81-07-2, Garantose, Saccharinol, Saccharinose, Gluside, o-Benzosulfimide, Benzoic sulfimide, Benzosulfinide, Benzosulphimide, Hermesetas, Saccharol, Glucid, Saccharin acid, Saccharin insoluble, o-Benzoyl sulfimide, Kandiset, Sacarina, Saccharina, Sucrette, Zaharina, 1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide, Sykose, Saxin, Sucre edulcor, o-Benzosulphimide, Benzoic sulphimide, Insoluble saccharin, 550 Saccharine, Benzo-2-sulphimide, o-Sulfobenzoic acid imide, o-Benzoic sulphimide, o-Benzoyl sulphimide, Sweeta, Benzoylsulfonic Imide, Natreen, Sacharin, 2-Sulphobenzoic imide, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 2,3-Dihydro-3-oxobenzisosulfonazole, Anhydro-o-sulfaminebenzoic acid, 2-Sulfobenzoic acid imide, Saccharin, insoluble, 3-Benzisothiazolinone 1,1-dioxide, 3-Hydroxybenzisothiazole S,S-dioxide, Benzoic acid sulfimide, 1,2-Dihydro-2-ketobenzisosulfonazole, Syncal, Benzo-sulphinide, Rcra waste number U202, Benzo[d]isothiazol-3(2H)-one 1,1-dioxide, Sacharin [Czech], 2,3-Dihydro-3-oxobenzisosulphonazole, Saccharin and salts, SACCHARIN SODIUM, 1,2-Dihydro-2-ketobenzisosulphonazole, Benzosulfimide, O-, Saccharin [USAN], Sulfobenzimide, O-, 1,2-Benzisothiazolin-3-one, 1,1-dioxide, 1,2-Benzothiazol-3(2H)-one 1,1-dioxide, o-Benzoic acid sulfimide, 1,1-dioxo-1,2-benzothiazol-3-one, 3-Hydroxybenzisothiazole-S,S-dioxide, RCRA waste no. U202, UNII-FST467XS7D, 1,1-Dioxide-1,2-benzisothiazolin-3-one, 1,2-Benzisothiazolin-3-one 1,1-dioxide, CCRIS 3707, CHEMBL310671, HSDB 669, CHEBI:32111, CVHZOJJKTDOEJC-UHFFFAOYSA-N, NSC 5349, NSC 5731, Saccharin-d4, Cristallose, Crystallose, Kristallose, Willosetten, EINECS 201-321-0, Madhurin, Sucromat, 1,1-Diox-1,2-benzisothiazol-3-one, 2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxide, Sodium saccharin, Saccharin soluble, Sodium saccharide, Sodium saccharine, Soluble saccharin, NCGC00094918-03, Saccharine soluble, 1,1-Dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one, E954, Saccharin, soluble, Sodium saccharinate, 1,2-Benzisothiazoline-3-one 1,1-dioxide, AI3-38107, 1,1-Dioxo-1,2-benzisothiazol-3(2H)-one, DSSTox_CID_1251, 1,1-Dioxide-1,2-benzisothiazol-3(2H)-one, o-Sulfonbenzoic acid imide sodium salt, DSSTox_RID_76039, 1,1-Dioxo-1,2-dihydro-benzo[d]isothiazol-3-one, DSSTox_GSID_21251, Saccharin, sodium salt, Sodium o-benzosulfimide, 2,3-Dihydro-1,2-benzoisothiazol-3-one-1,1-dioxide, Saccharin (only persons who manufacture are subject, no supplier notification), CAS-81-07-2, NSC4867, NSC5731, 2-hydrobenzo[d]isothiazole-1,1,3-trione, 128-44-9, Artificial sweetening substanz gendorf 450, Glycophenol, Neosaccharin, Benzo-2-sulfiide, O-Benzoylsulfimide, Saccharin nitranion, 2-Sulfobenzoicimide, Ortho sulphobenzamide, O-Sulfobenzoic imide, Sweeta (TN), 2-Sulfobenzoic imide, Tolunene-2-sulfonamide, Spectrum_000213, 6381-61-9, Saccharin (JP15/NF), Saccharin (JP16/NF), Spectrum2_001432, Spectrum3_001475, Spectrum4_000449, Spectrum5_001181, WLN: T56 BSWMVJ, AC1L1JP6, SCHEMBL3816, FST467XS7D, NCIOpen2_005140, NCIOpen2_005180, BSPBio_003029, KBioGR_000838, KBioSS_000693, ARONIS27195, DivK1c_000164, SPECTRUM1501171, SPBio_001564, 109185_ALDRICH, 240931_ALDRICH, GTPL5432, CHEMBL1709040, 12475_FLUKA, BDBM29278, HMS500I06, KBio1_000164, KBio2_000693, KBio2_003261, KBio2_005829, KBio3_002529, NSC5349, 2q38, MolPort-000-881-701, NINDS_000164, BB_SC-3628, HMS1921N03, HMS2092J09, Pharmakon1600-01501171, NSC-5349, ZINC2560357, 3-Benzisothiazolinone 1, 1-dioxide, Tox21_111358, Tox21_201880, Tox21_302950, BBL015343, CCG-39011, DNC008189, NSC757878, SBB027246, STK803263, 2, 3-Dihydro-3-oxobenzisosulfonazole, 2,3-Dihydro-3-oxo-Benzisosulfonazole, AKOS000120481, AKOS017272711, Tox21_111358_1, 1, 2-Dihydro-2-ketobenzisosulfonazole, LS-1805, MCULE-3632531025, NSC-757878, RP24399, IDI1_000164, Benzisosulfonazole, 2,3-dihydro-3-oxo-, NCGC00094918-01, NCGC00094918-02, NCGC00094918-04, NCGC00094918-05, NCGC00094918-06, NCGC00094918-07, NCGC00256329-01, NCGC00259429-01, AJ-40561, AK129019, AN-23015, AN-24035, BAS 00293362, BC650677, HE039324, HE362035, HE391043, KB-60378, SC-18191, ST073992, 1.2 -benzoisothiazole-3-on 1.1-dioxide, 1, 2-Benzisothiazolin-3-one 1,1-dioxide, ST2412651, 1,2-benzisothiazol-3(2H)-one-1,1-dioxide, B0004, FT-0674493, H2947, Z1771, 1,2-Benzisothiazol-3(2H)-one -1,1-dioxide, C12283, D01085, 1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide, 10362-EP2272822A1, 10362-EP2277848A1, 10362-EP2277865A1, 10362-EP2277879A1, 10362-EP2284157A1, 10362-EP2287167A1, 10362-EP2289883A1, 10362-EP2289892A1, 10362-EP2295426A1, 10362-EP2295427A1, 10362-EP2295429A1, 10362-EP2298735A1, 10362-EP2298764A1, 10362-EP2298765A1, 10362-EP2301536A1, 10362-EP2301538A1, 10362-EP2305248A1, 10362-EP2305254A1, 10362-EP2305257A1, 10362-EP2305648A1, 10362-EP2305663A1, 10362-EP2305668A1, 10362-EP2305688A1, 10362-EP2308867A2, 10362-EP2308870A2, 10362-EP2311455A1, 10362-EP2311821A1, 10362-EP2311824A1, 10362-EP2311829A1, 10362-EP2311842A2, 10362-EP2314584A1, 10362-EP2314588A1, 10362-EP2314590A1, 10362-EP2316452A1, 10362-EP2374792A1, 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide, 88543-EP2275422A1, 88543-EP2277868A1, 88543-EP2277869A1, 88543-EP2277870A1, 88543-EP2298076A1, 88543-EP2298077A1, 88543-EP2301353A1, 88543-EP2305031A1, 88543-EP2305034A1, 88543-EP2305035A1, 88543-EP2374791A1, AB00052233-04, 144417-EP2289518A1, 144417-EP2292231A1, 1,1-Dioxido-3-oxo-2,3-dihydrobenzo[d]isothiazole, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9CI, 2,3-dihydro-1,2-benzisothiazol-3-one-1,1-dioxide, 2,3-dihydro-1lambda,2-benzothiazole-1,1,3-trione, 2,3-dihydro-3-oxo-1,2-benzisothiazol-1,1-dioxide, T5883772, W-200289, 03AC8EC2-D02A-464C-A7C3-7CABD643CC1E, 2,3-dihydro-1$l;{6},2-benzothiazole-1,1,3-trione, I14-62592, 1, 2-Benzisothiazolin-3-one, 1,1-dioxide, sodium salt, 1, 2-Benzothiazol-3(2H)-one 1,1-dioxide sodium salt, 1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide, sodium salt, 1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one, SACCHARIN (229 degrees C) MELTING POINT STANDARD, WHO STANDARD, InChI=1/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9, 126987-83-5, 474-91-9, 61255-27-4, 890126-34-8

Removed Synonyms

Stilalgin, Saccharin calcium, Saccharin, sodium, Calcium, Saccharin, 1,1-dioxide, 1, 1,1-dioxide, CID5143, C1454, Sodium 1,2 benzisothiazolin-3-one 1,1-dioxide, D012439, 5-Bromobenzo[d]isothiazol-3(2H)-one 1,1-dioxide, LSA, 88-19-7, SAC

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