Dimethyl acetylenedicarboxylate → HCID 12437416, compound

HRID 614176Notes

Reaction equation

HRID 614176 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 (2X) gave little improvement in purity. The brown solid as decolorized in ethyl acetate solution and recrystallized (3X) 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 (2X)
  3. customgave little improvement in purity
  4. customrecrystallized (3X)

Sources & evidence

ORD record
ord-115c8ba374934855809c26cc0094f63f
Source dataset
uspto-grants-1979_03
Patent number
US04144047

Reaction notes

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