Trifluoroacetic acid → 2-(3,4-Dichloro-N-methylphenylsulfonamido)-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylic acid

HRID 1642126Notes

Reaction equation

HRID 1642126 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[C:11]([S:16]([N:19]([C:21]2[S:25][C:24]3[CH2:26][CH2:27][CH2:28][CH2:29][C:23]=3[C:22]=2[C:30]([O:32]C(C)(C)C)=[O:31])[CH3:20])(=[O:18])=[O:17])[CH:12]=[CH:13][C:14]=1[Cl:15]>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[C:11]([S:16]([N:19]([C:21]2[S:25][C:24]3[CH2:26][CH2:27][CH2:28][CH2:29][C:23]=3[C:22]=2[C:30]([OH:32])=[O:31])[CH3:20])(=[O:17])=[O:18])[CH:12]=[CH:13][C:14]=1[Cl:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66756439tert-Butyl 2-(3,4-dichloro-N-methylphenylsulfonamido)-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylate

Product 1

HCID 667559492-(3,4-Dichloro-N-methylphenylsulfonamido)-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (30 ml, 404 mmol) was added to a solution of tert-butyl 2-(3,4-dichloro-N-methylphenylsulfonamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (8.00 g, 16.8 mmol) in DCM (100 ml), and stirring was carried out for 1 h at room temperature. The reaction mixture was concentrated, and the TFA that remained was removed with toluene, DCM and diethyl ether. The residue was washed twice with diisopropyl ether.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe TFA that remained was removed with toluene, DCM and diethyl ether
  3. washThe residue was washed twice with diisopropyl ether

Sources & evidence

ORD record
ord-e21f8a6b45b64f66a965340f4be424db
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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