Hydrochloric Acid → 2-(4,5,7-trifluorobenzothiazol-2-ylthio)-N-phenylacetamide

HRID 1940620Notes

Reaction equation

HRID 1940620 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[F:12][C:13]1[C:18]2[N:19]=[C:20]([SH:22])[S:21][C:17]=2[C:16]([F:23])=[CH:15][C:14]=1[F:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl>O.CS(C)=O>[F:12][C:13]1[C:18]2[N:19]=[C:20]([S:22][CH2:2][C:3]([NH:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:4])[S:21][C:17]=2[C:16]([F:23])=[CH:15][C:14]=1[F:24]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11485ChloroacetanilideHCID 178505914HCID 178505914, compound

Product 1

HCID 214635402-(4,5,7-trifluorobenzothiazol-2-ylthio)-N-phenylacetamideYield 54.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To DMSO (15 ml) was added α-chloroacetoanilide (850 mg, 5 mmol), 4,5,7-trifluoro-2-mercaptobenzothiazole (1.1 g, 5 mmol), potassium carbonate (690 mg, 5 mmol) and potassium iodide (50 mg) and the mixture was stirred at room temperature for 4 hours. The resultant reaction mixture was diluted with water, acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried and then evaporated to yield a crude product, which was purified on a silica gel column to give 2-(4,5,7-trifluorobenzothiazol-2-ylthio)-N-phenylacetamide (0.97 g, 52%).

Workup

  1. customThe resultant reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated
  6. customto yield a crude product, which
  7. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-ee2697d21caa4e5999c13043483e5995
Source dataset
uspto-grants-1997_12
Patent number
US05700819

Reaction notes

Loading…