Hydrochloric Acid → Methyl 4-(chlorosulfonyl)thiophene-3-carboxylate

HRID 28013Notes

Reaction equation

HRID 28013 reaction equation
[Cl:1][S:2]([C:5]1[C:6]([C:10](Cl)=[O:11])=[CH:7][S:8][CH:9]=1)(=[O:4])=[O:3].[CH3:13][OH:14].Cl>C(Cl)(Cl)Cl>[CH3:13][O:14][C:10]([C:6]1[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])=[CH:9][S:8][CH:7]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 54034905HCID 54034905, compound

Product 1

HCID 12593671Methyl 4-(chlorosulfonyl)thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

44.1 G. (0.18 mol) of the obtained 4-chlorosulfonylthiophene-3-carboxylic acid chloride are dissolved in 450 ml. of absolute chloroform, 9.6 g. (0.3 mol) of absolute methanol are added and the solution is heated to reflux for 9 hours [until termination of the hydrogen chloride evolution]. The mixture is then evaporated to dryness in vacuo, the residue crystallizing out. There is obtained 4-chlorosulfonylthiophene-3-carboxylic acid methyl ester, which can be converted into the 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-thieno[3,4-e]-1,2-thiazine-3-carboxamide 1,1-dioxide in a manner analogous to that described in the last four paragraphs of Example 5.

Workup

  1. temperaturethe solution is heated
  2. customThe mixture is then evaporated to dryness in vacuo
  3. customthe residue crystallizing out

Sources & evidence

ORD record
ord-fbcbedba24414a70851df1b34584ce1c
Source dataset
uspto-grants-1980_09
Patent number
US04224445

Reaction notes

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