Sodium Chloride → tert-Butyl 2-(3,4-dichloro-N-methylphenylsulfonamido)-4,5,6,7-tetrahydrobenzo-[b]thiophene-3-carboxylate

HRID 1642125Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[S:17][C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[C:14]=2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:29]([O-])([O-])=O.[K+].[K+].CI.[Na+].[Cl-]>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([C:13]2[S:17][C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[C:14]=2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH3:29])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 40 °C

Procedure

tert-Butyl 2-(3,4-dichlorophenylsulfonamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (21.64 g, 46.8 mmol) was dissolved in acetone (200 ml), and K2CO3 (12.9 g, 93.6 mmol) was added thereto. Methyl iodide (5.83 ml, 93.6 mmol) was then added, and the suspension was heated overnight at 40° C. After cooling to room temperature, water and saturated NaCl solution were added and the product was extracted with ethyl acetate. The organic phase was dried (sodium sulfate) and the product was purified by crystallization from methanol.

Workup

temperatureAfter cooling to room temperature
extractionthe product was extracted with ethyl acetate
dry with materialThe organic phase was dried (sodium sulfate)
customthe product was purified by crystallization from methanol

Sources & evidence

ORD record: ord-9ad16240addf439ea3b53b7601ff98fa
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119633B2

Reaction notes

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