Dimethyl acetylenedicarboxylate → Dimethyl 3-(m-Tolyl)-4,5-Isothiazoledicarboxylate

HRID 614177Notes

Reaction equation

HRID 614177 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2OC(=O)[S:9][N:8]=2)[CH:2]=1.[C:14]([C:20]([O:22][CH3:23])=[O:21])#[C:15][C:16]([O:18][CH3:19])=[O:17]>ClC1C=CC=CC=1>[C:1]1([CH3:13])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([C:20]([O:22][CH3:23])=[O:21])[S:9][N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 124373965-(3-Methylphenyl)-2H-1,3,4-oxathiazol-2-one

Product 1

HCID 12437411Dimethyl 3-(m-Tolyl)-4,5-IsothiazoledicarboxylateYield 52.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

5-m-Tolyl-1,3,4-oxathiazol-2-one (19.32 g, 0.1 mol) and dimethyl acetylenedicarboxylate (28.42 g, 0.2 mol) were heated at reflux in 60 ml of chlorobenzene as given above. After the initial crystallization from cold methanol, three recrystallization from diethyl ether/petroleum ether gave 15.18 g (0.0522 mol, 52.2%) of white solid, m.p. 53°-54.5°.

Workup

  1. customAfter the initial crystallization
  2. customfrom cold methanol, three recrystallization from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-cac1fa4a6ccd4fcdaae3faa14ee2c93c
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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