Benzenesulfonyl chloride → Ethyl 2-(benzenesulfonamido)-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate

HRID 1506897Notes

Reaction equation

HRID 1506897 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][CH2:14][CH3:15])=[O:12].[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1.O>[C:16]1([S:22]([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][CH2:14][CH3:15])=[O:12])(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Product 1

HCID 391240Ethyl 2-(benzenesulfonamido)-4,5,6,7-tetrahydrobenzothiophene-3-carboxylateYield 41.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.113 g) was added to a solution of benzenesulphonyl chloride (0.097 g) in pyridine (5 ml) and the resultant solution was stirred at room temperature for 16 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with hydrochloric acid (1M), water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane (5%) to give ethyl 2-benzenesulphonylamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.076 g) as a pale yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with hydrochloric acid (1M), water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of ethyl acetate and pentane (5%)

Sources & evidence

ORD record
ord-4e569a7428234ed9a1103146c9171479
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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