Dimethyl acetylenedicarboxylate → Dimethyl 3-methyl-1,2-thiazole-4,5-dicarboxylate

HRID 1050784Notes

Reaction equation

HRID 1050784 reaction equation
[CH3:1][C:2]1OC(=O)[S:4][N:3]=1.[CH3:8][O:9][C:10]([C:12]#[C:13][C:14]([O:16][CH3:17])=[O:15])=[O:11]>ClC1C=CC=CC=1>[CH3:8][O:9][C:10]([C:12]1[C:2]([CH3:1])=[N:3][S:4][C:13]=1[C:14]([O:16][CH3:17])=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 10313121HCID 10313121, compound

Product 1

HCID 12437421Dimethyl 3-methyl-1,2-thiazole-4,5-dicarboxylateYield 53.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 5-Methyl-[1,3,4]oxathiazol-2-one (37.94 mmol) and dimethylacetylenedicarboxylate (75.89 mmol) in chlorobenzene (22.3 mL) was refluxed with stirring for 6 h before the mixture was concentrated in vacuo. Distillation of the residue gave the desired product (4.38 g) at by 100-105° C. (1.0 Torr) as an oil: MS (m/z) 216.0 (M+1).

Workup

  1. concentrationwas concentrated in vacuo
  2. distillationDistillation of the residue

Sources & evidence

ORD record
ord-233cfa4daff64bc699a305db80fd2b74
Source dataset
uspto-grants-2016_07
Patent number
US09387200B2

Reaction notes

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