Hydrochloric Acid → 5-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-one

HRID 1080612Notes

Reaction equation

HRID 1080612 reaction equation
Cl[C:2]([S:4]Cl)=[O:3].[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][CH:9]=1.Cl>>[CH3:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]2[O:13][C:2](=[O:3])[S:4][N:14]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 75990(Chlorothio)formyl chlorideHCID 769594-Methoxybenzamide

Product 1

HCID 8194565-(4-Methoxyphenyl)-1,3,4-oxathiazol-2-oneYield 64.1%

Procedure

Chlorocarbonyl sulphenyl chloride (13.2 g, 0.10 mol) is added dropwise to a stirred solution of 4-methoxybenzamide (13.8 g, 0.091 mol) under dry nitrogen at room temperature. When the addition is complete, the mixture is refluxed for 8 hours, during which time hydrogen chloride gas is evolved. The solution is allowed to cool to room temperature and the solvent is removed in vacuo. The residue is triturated with methyl tert.-butyl ether and the crystalline solid is filtered off and dried, to give 5-(4-methoxyphenyl)-[1,3,4]oxathiazolin-2-one (12.2 g, 64%) as colourless crystals, m.p. 117°-118° C.

Workup

  1. additionWhen the addition
  2. customthe solvent is removed in vacuo
  3. customThe residue is triturated with methyl tert.-butyl ether
  4. filtrationthe crystalline solid is filtered off
  5. customdried

Sources & evidence

ORD record
ord-0b89400919de454cafaf08e3d35734fb
Source dataset
uspto-grants-1996_12
Patent number
US05583092

Reaction notes

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