4-t-Butylbenzenesulfonyl chloride → Methyl 3-(4-tert-butylphenylsulfonamido)benzo[b]thiophene-2-carboxylate

HRID 1925724Notes

Reaction equation

HRID 1925724 reaction equation
[NH2:1][C:2]1[C:3]2[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:15]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>N1C=CC=CC=1>[C:15]([C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:1][C:2]2[C:3]3[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=3[S:5][C:6]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:27])=[O:26])=[CH:21][CH:20]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 874720Methyl 3-aminobenzo[b]thiophene-2-carboxylate

Product 1

HCID 59180462Methyl 3-(4-tert-butylphenylsulfonamido)benzo[b]thiophene-2-carboxylateYield 29.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution methyl 3-aminobenzo[b]thiophene-2-carboxylate (0.207 g; 1 mmol) in pyridine (1 mL) was added 4-tert-butylbenzenesulfonyl chloride (0.256 g; 1.1 mmol). The resulting mixture was stirred at room temperature for 36 hours and then partitioned between dichloromethane and aqueous hydrochloric acid (2N). The organic layer was separated, dried over sodium sulfate, filtered through a pad of silica gel, and concentrated under reduced pressure to give the desired product as a yellow solid (120 mg).

Workup

  1. custompartitioned between dichloromethane and aqueous hydrochloric acid (2N)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a3230318c6a4d0c88daf4351014166f
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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