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

HRID 443707Notes

Reaction equation

HRID 443707 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-0175d03f10284ab289d3f61baf74f039
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

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