Hydrochloric Acid → 2-Sulfamoyl-1,3-benzothiazol-6-yl dimethylcarbamate

HRID 2418290Notes

Reaction equation

HRID 2418290 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.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:15][N:16]([CH3:20])[C:17](=[O:18])[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl Chloride2×HCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 444619572-Sulfamoyl-1,3-benzothiazol-6-yl dimethylcarbamateYield 76,325.203%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (2.3 g, 0.01 mole) and 4-dimethylaminopyridine (200 mg) in pyridine (25 ml) was added dimethylcarbamoyl chloride (0.95 ml, 0.01 mmole). After stirring for 18 hours additional dimethylcarbamoyl chloride (1.5 ml) was added and stirring was continued for 18 hours. The reaction mixture was poured into ice water and excess hydrochloric acid to give 2.3 g of (2-sulfamoyl-6-benzothiazolyl) N,N-dimethylcarbamate which melts at 208°-209° C. after recrystallization from 2-propanol.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-33a5ebb4954e46929f019ad73b6f61d9
Source dataset
uspto-grants-1984_09
Patent number
US04472417

Reaction notes

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