Methanol → Methyl 3-(chlorosulfonyl)-1-benzothiophene-2-carboxylate

HRID 128257Notes

Reaction equation

HRID 128257 reaction equation
Cl[C:2]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[S:13]([Cl:16])(=[O:15])=[O:14])=[O:3].[CH3:17][OH:18]>C(Cl)(Cl)Cl>[CH3:17][O:18][C:2]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[C:5]=1[S:13]([Cl:16])(=[O:14])=[O:15])=[O:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 536526182-Chlorocarbonyl-benzo[b]thiophene-3-sulfonic acid chloride

Product 1

HCID 13178319Methyl 3-(chlorosulfonyl)-1-benzothiophene-2-carboxylateYield 53.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

168.0 gm (0.569 mol) of 2-chlorocarbonyl-benzo[b]thiophene-3-sulfonic acid chloride were dissolved in 1 liter of anhydrous chloroform, and the solution was admixed with 27.5 gm (0.858 mol) of dry methanol and refluxed for 3 hours. The reaction mixture was evaporated in vacuo, and the residue was recrystallized twice from a little methanol, yielding 88.5 gm (53.5% of theory) of colorless 2-methoxycarbonyl-benzo[b]-thiophene-3-sulfonic acid chloride. M.p.: 100°-101° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was recrystallized twice from a little methanol

Sources & evidence

ORD record
ord-00cedcb406b946fcbe4da1a8cf8c94cf
Source dataset
uspto-grants-1981_03
Patent number
US04259336

Reaction notes

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