Dimethyl acetylenedicarboxylate → HCID 12437419, compound

HRID 1448676Notes

Reaction equation

HRID 1448676 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2OC(=O)[S:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:15]([C:21]([O:23][CH3:24])=[O:22])#[C:16][C:17]([O:19][CH3:20])=[O:18]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([C:21]([O:23][CH3:24])=[O:22])[S:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 12437402HCID 12437402, compound

Product 1

HCID 12437419HCID 12437419, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

5-(3,4-Dichlorophenyl)-1,3,4-oxathiazol-2-one (99.2 g, 0.4 mol) and dimethyl acetylenedicarboxylate (113.5 g, 0.8 mol) were heated in 240 ml of chlorobenzene at reflux for 47 hours. The product, from hot methanol, was recrystallized twice from hot methanol to give 97.8 g (0.283 mol, 70.7%) of white solid, m.p. 105°-107°.

Workup

  1. temperatureat reflux for 47 hours
  2. customThe product, from hot methanol, was recrystallized twice from hot methanol

Sources & evidence

ORD record
ord-a339b53132fe4bcdab61799cfff8f1aa
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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