Hydrochloric Acid → Ethyl(2-sulfamoyl-6-benzothiazolyl)carbonate

HRID 615600Notes

Reaction equation

HRID 615600 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.[CH2:15]([O:17][C:18](Cl)=[O:19])[CH3:16].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[CH3:16][CH2:15][O:17][C:18]([O: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)=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 20426472Ethyl(2-sulfamoyl-6-benzothiazolyl)carbonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (3.45 g 0.015 mole) and 4-dimethylaminopyridine (200 mg) in pyridine (25 ml) was added ethylchloroformate (1.9 ml). The reaction mixture was stirred at 25° C. for 2 hours, poured into ice and excess hydrochloric acid, extracted with ethyl acetate, washed with water, dried over magnesium sulfate and chromatographed after evaporation of the solvent on silica (150 g, 70-230 mesh) eluting with ethyl acetate-hexane 1:1 (v/v) to obtain 1.3 g of ethyl(2-sulfamoyl-6-benzothiazolyl)carbonate which melts at 144°-6° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customchromatographed
  5. customafter evaporation of the solvent on silica (150 g, 70-230 mesh)
  6. washeluting with ethyl acetate-hexane 1:1 (v/v)

Sources & evidence

ORD record
ord-668a415e97984b59933ca151678a1899
Source dataset
uspto-grants-1985_02
Patent number
US04500538

Reaction notes

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