Hydrochloric Acid → 2-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

HRID 28008

Reaction equation

HRID 28008 reaction equation
[Cl:1][S:2]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[C:10](Cl)=[O:11])(=[O:4])=[O:3].[CH3:13][OH:14].Cl>C(Cl)(Cl)Cl>[CH3:13][O:14][C:10]([C:6]1[S:7][CH:8]=[CH:9][C:5]=1[S:2]([Cl:1])(=[O:4])=[O:3])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13755631HCID 13755631, compound

Product 1

HCID 27367332-Thiophenecarboxylic acid, 3-(chlorosulfonyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

48 G. (0.196 mol) of the obtained 3-chlorosulfonylthiophene-2-carboxylic acid chloride are dissolved in 500 ml. of absolute chloroform, 9.6 g. (0.3 mol) of absolute methanol are added and the solution is heated to reflux for 3 hours [until no more hydrogen chloride evolution]. The mixture is evaporated to dryness in vacuo and the residue allowed to crystallize out. There is obtained pure 3-chlorsulfonylthiophene-2-carboxylic acid methyl ester. 2.41 G. (0.010 mol) of the obtained 3-chlorosulfonylthiophene-2-carboxylic acid methyl ester are dispersed together with 1.53 g. of sarcosine ethyl ester hydrochloride in 10 ml. of absolute pyridine and stirred at room temperature. After 2 hours, the mixture is poured on to 50 ml. of ice-cold 2-N hydrochloric acid and extracted five times with 20 ml. of methylene chloride each time. The combined organic phases are dried over sodium sulfate, filtered and evaporated. The crystalline residue is digested with a small amount of ice-cold ethanol.

Workup

  1. temperaturethe solution is heated
  2. customThe mixture is evaporated to dryness in vacuo
  3. customto crystallize out

Sources & evidence

ORD record
ord-ccb1cf14c4f44945b582c0fb637e86e5
Source dataset
uspto-grants-1980_09
Patent number
US04224445

Linked notes

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