Hydrochloric Acid → HCID 12045145, compound

HRID 1790224Notes

Reaction equation

HRID 1790224 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:27]=[CH:26][C:17]2[S:18][C:19]([S:22](Cl)(=[O:24])=[O:23])=[C:20]([CH3:21])[C:16]=2[CH:15]=1.Cl>N1C=CC=CC=1>[Cl:13][C:14]1[CH:27]=[CH:26][C:17]2[S:18][C:19]([S:22]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=3)(=[O:23])=[O:24])=[C:20]([CH3:21])[C:16]=2[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 12045145HCID 12045145, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 3 mL of pyridine was dissolved 60 mg of ethyl 4-aminobenzoate, and 123 mg of 5-chloro-2-chlorosulfonyl-3-methylbenzo[b]thiophene was added at 0° C., followed by 2 hours of stirring at room temperature. After confirmation of disappearance of the starting material, 2 mol/L hydrochloric acid was added, followed by extraction with ether. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane=1/3) to obtain 80 mg of the title compound as light pink powder.

Workup

  1. additionwas added at 0° C.
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-e7b088af0aa04e6893ff19a8160fc6c1
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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