Water → tert-Butyl 2-(3,4-dichlorophenylsulfonamido)-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate

HRID 1642124

Reaction equation

HRID 1642124 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].N1C=CC=CC=1.[Cl:24][C:25]1[CH:26]=[C:27]([S:32](Cl)(=[O:34])=[O:33])[CH:28]=[CH:29][C:30]=1[Cl:31].O>C(Cl)Cl>[Cl:24][C:25]1[CH:26]=[C:27]([S:32]([NH:1][C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]=2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=[O:33])=[O:34])[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 10777280tert-Butyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Product 1

HCID 86625455tert-Butyl 2-(3,4-dichlorophenylsulfonamido)-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (12.26 g, 48.4 mmol) was dissolved in DCM (150 ml), and pyridine (6.0 ml, 74 mmol) was added thereto. A solution of 3,4-dichlorobenzenesulfonyl chloride (8.4 ml, 54 mmol) was then added, and the mixture was heated for 17 h under reflux and then cooled to room temperature. Water was added (100 ml), and stirring was carried out overnight at room temperature. The phases were then separated (pH organic phase≈2), washed with saturated NaHCO3 solution, dried (sodium sulfate) and concentrated in vacuo.

Workup

  1. temperaturethe mixture was heated for 17 h
  2. temperatureunder reflux
  3. customThe phases were then separated (pH organic phase≈2),
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b9e7296bb0049d68a884740daff09a0
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Linked notes

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