Hydrochloric Acid → (2-Sulfamoyl-6-benzothiazolyl) N,N-dimethylsulfamate

HRID 2418292Notes

Reaction equation

HRID 2418292 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9]([NH2:12])(=[O:11])=[O:10])[S:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25].Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:22][N:23]([CH3:28])[S:24](=[O:26])(=[O:25])[O:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([S:9](=[O:11])(=[O:10])[NH2:12])[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 44346124(2-Sulfamoyl-6-benzothiazolyl) N,N-dimethylsulfamate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (2.3 g, 0.01 mole), triethylamine (1.4 ml) and 4-dimethylaminopyridine (200 mg) in dimethylformamide (20 ml) was added dimethylsulfamoyl chloride (1.1 ml). The reaction mixture was heated on a steam bath for 18 hours, poured into ice water and excess hydrochloric acid, extracted into ethyl acetate, washed with water and dried over magnesium sulfate. The ethyl acetate was evaporated and the (2-sulfamoyl-6-benzothiazolyl) N,N-dimethylsulfamate purified by chromatography on a 2 mm preparative silica gel TLC plate developed with chloroform/methanol 9:1 (v/v) m.p.=162°-164° C.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath for 18 hours
  2. extractionextracted into ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe ethyl acetate was evaporated
  6. customthe (2-sulfamoyl-6-benzothiazolyl) N,N-dimethylsulfamate purified by chromatography on a 2 mm preparative silica gel TLC plate

Sources & evidence

ORD record
ord-2f2efebd2eb4444fab58d376ce37a6a0
Source dataset
uspto-grants-1984_09
Patent number
US04472418

Reaction notes

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