Hydrochloric Acid → 2-Sulfamoyl-6-benzothiazolyl 2-(4-chlorophenyl)acetate

HRID 1649382Notes

Reaction equation

HRID 1649382 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.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](Cl)=[O:31])=[CH:25][CH:24]=1.Cl>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:1][C:2]2[CH:14]=[CH:13][C:5]3[N:6]=[C:7]([S:9](=[O:11])(=[O:10])[NH2:12])[S:8][C:4]=3[CH:3]=2)=[O:31])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 132366542-Sulfamoyl-6-benzothiazolyl 2-(4-chlorophenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-hydroxy-2-benzothiazolesulfonamide (1.15 g., 0.005 mole) triethylamine (0.7 ml, 0.005 mole) and 4-dimethylaminopyridine (5 mg, catalyst) in dimethylformamide (10 ml) is added 2-(4-chlorophenyl)acetyl chloride (0.8 ml). The reaction mixture is stirred for 2 hours, poured into ice water, acidified with hydrochloric acid and extracted with ether. The organic extract is washed with water and dried over magnesium sulfate. The ether is distilled at reduced pressure and the residue chromatographed on silica gel as eluant (130 g, 70-230 mesh) using ethylacetatehexane (1:1) to give 2-sulfamoyl-6-benzothiazolyl 2-(4-chlorophenyl)acetate which melts at 206°-208° C. after recrystallization from benzene.

Workup

  1. extractionextracted with ether
  2. extractionThe organic extract
  3. washis washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationThe ether is distilled at reduced pressure
  6. customthe residue chromatographed on silica gel as eluant (130 g, 70-230 mesh)

Sources & evidence

ORD record
ord-e5bf4f0263e04b14bb756354993ff42c
Source dataset
uspto-grants-1983_11
Patent number
US04416890

Reaction notes

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