Benzenesulfonyl chloride → HCID 86693763, compound

HRID 1506900Notes

Reaction equation

HRID 1506900 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH: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>[C:16]1([S:22]([N:1]([S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])[C:2]2[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH: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

4

Reactant 2

HCID 7369Benzenesulfonyl chloride2×HCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylate

Product 1

HCID 86693763HCID 86693763, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-aminobenzo(b)thiophene-3-carboxylate (0.165 g) and benzenesulphonyl chloride (0.53 g) in pyridine (7 ml) was stirred and heated at 80° C. for 5 hours. Further benzenesulphonyl chloride (0.53 g) was added and the mixture was stirred and heated at 80° C. for 24 hours. The mixture was concentrated and the residue was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with 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 (5-10%) to give ethyl 2-[bis-(benzenesulphonyl)amino]benzo[b]thiophene-3-carboxylate (0.173 g) as a colourless oil.

Workup

  1. stirringthe mixture was stirred
  2. temperatureheated at 80° C. for 24 hours
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionThe aqueous layer was further extracted with ethyl acetate
  6. washthe combined organic layers were washed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane (5-10%)

Sources & evidence

ORD record
ord-075c87bff6a9458f92331a4645cf82ee
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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