Dimethyl acetylenedicarboxylate → HCID 11033155, compound

HRID 1050783Notes

Reaction equation

HRID 1050783 reaction equation
[C:1]1([C:7]2OC(=O)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][O:14][C:15]([C:17]#[C:18][C:19]([O:21][CH3:22])=[O:20])=[O:16]>ClC1C=CC=CC=1>[CH3:13][O:14][C:15]([C:17]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][S:9][C:18]=1[C:19]([O:21][CH3:22])=[O:20])=[O:16]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 8531705-phenyl-1,3,4-oxathiazol-2-one

Product 1

HCID 11033155HCID 11033155, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 5-phenyl-[1,3,4]oxathiazol-2-one (30.33 mmol) and dimethylacetylenedicarboxylate (60.67 mmol) in chlorobenzene (17.8 mL) was refluxed with stirring for 6 h before it was concentrated in vacuo. The residue was crystallized from cold MeOH to give the title compound (5.0 g) as a slightly yellow solid: MS (m/z) 278.1 (M+1).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was crystallized from cold MeOH

Sources & evidence

ORD record
ord-8d3eb03966d143339f3bb04e04b4ebf6
Source dataset
uspto-grants-2016_07
Patent number
US09387200B2

Reaction notes

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