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

HRID 1448679Notes

Reaction equation

HRID 1448679 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 recrystallizations 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 recrystallizations from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-143e3ce5bcfa4ba6ad37e91545bebc70
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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