Dimethyl acetylenedicarboxylate → HCID 12437416, compound

HRID 443706Notes

Reaction equation

HRID 443706 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3]([O:5][CH3:6])=[O:4].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2OC(=O)[S:22][N:21]=2)=[CH:16][CH:15]=1)([O-:13])=[O:12]>C(OCC)(=O)C>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:1]([C:7]([O:9][CH3:10])=[O:8])[S:22][N:21]=2)=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 12437399(4-Nitrophenyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 12437416HCID 12437416, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl acetylenedicarboxylate (85.26 g, 0.6 mol) and 5-(p-nitrophenyl)-1,3,4-oxathiazol-2-one (33.63 g, 0.15 mol) were heated as given above for 15 hours. Crystallization of the brown solid from methanol (2×) gave little improvement in purity. The brown solid was decolorized in ethyl acetate solution and recrystallized (3×) to give 12.2 g (0.0378 mol, 25.2%) of dark gold solid, m.p. 142°-143°.

Workup

  1. customas given above for 15 hours
  2. customCrystallization of the brown solid from methanol (2×)
  3. customgave little improvement in purity
  4. customrecrystallized (3×)

Sources & evidence

ORD record
ord-c673154c7dda4eed83d367da90c5052a
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

Loading…