Methanol → Methyl 4-amino-3-isothiazolecarboxylate hydrochloride

HRID 2073409Notes

Reaction equation

HRID 2073409 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:8]([OH:10])=[O:9])=[N:5][S:6][CH:7]=1.S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[NH2:2][C:3]1[C:4]([C:8]([O:10][CH3:15])=[O:9])=[N:5][S:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 66031414-Aminoisothiazole-3-carboxylic acid hydrochloride

Product 1

HCID 13726721Methyl 4-amino-3-isothiazolecarboxylate hydrochloride

Procedure

A suspension of 52.0 g of 4-amino-3-isothiazolecarboxylic acid hydrochloride [prepared by the method of K. Gewald and P. Billman, Liebigs Ann. 1542 (1979)] in 300 ml methanol was cooled in an ice-bath and 10 ml of thionyl chloride was added dropwise. The reaction mixture was refluxed 3 hours, cooled and the solvent evaporated. The residual solid was collected, washed with ether and dried giving 47.5 g of methyl 4-amino-3-isothiazolecarboxylate hydrochloride, m.p. 170°(d).

Workup

  1. customprepared by the method of K
  2. temperatureThe reaction mixture was refluxed 3 hours
  3. temperaturecooled
  4. customthe solvent evaporated
  5. customThe residual solid was collected
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-9736b9d140a242b69b4909cd3eb94f55
Source dataset
uspto-grants-1990_04
Patent number
US04917719

Reaction notes

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