Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate → HCID 68278820, compound

HRID 1506916Notes

Reaction equation

HRID 1506916 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:15][C:16]1[S:20][C:19]2[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=2[C:17]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]>N1C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:15][C:16]1[S:20][C:19]2[CH2:21][CH2:22][CH2:23][CH2:24][C:18]=2[C:17]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylateHCID 1366162-Trifluoromethylbenzenesulphonyl chloride

Product 1

HCID 68278820HCID 68278820, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Trifluoromethylbenzenesulphonyl chloride (0.195 g) was added to a solution of ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.150 g) in pyridine (1.7 ml) at room temperature and the resultant mixture was stirred for 64 hours. The solvent was removed and the residue was purified directly by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-(2-trifluoromethylbenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.194 g) as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified directly by chromatography on silica
  3. washeluting with a mixture of ethyl acetate and cyclohexane (0-20%)

Sources & evidence

ORD record
ord-01ef2f0cd627464bbf87df78cae54dd5
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

Loading…