Methyl propiolate → HCID 178516414, compound

HRID 725770Notes

Reaction equation

HRID 725770 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:16](OC)(=[O:19])[C:17]#[CH:18]>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:18]=[CH:17][C:16]([OH:19])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 13536Methyl propiolateHCID 70624(4-Chlorophenyl)hydrazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 178516414HCID 178516414, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

A solution of 57.5 g of 4-chlorophenylhydrazine hydrosulfate in 1,000 ml of tert-butanol was first treated in portions with 100.8 g of potassium tert-butoxide and then (after stirring for 10 min) in the course of 45 min at 45° C.-50° C. with a solution of 27.7 g of methyl propiolate in 90 ml of tertbutanol. After 1 h at boiling point, the mixture was allowed to cool and the solvent was removed under reduced pressure. The residue thus obtained was dissolved in 1,200 ml of water. The aqueous phase was first washed with methylene chloride and then acidified, the product being deposited as a solid. 47.6 g of the title compound were obtained, m.p.: 185°-187° C.

Workup

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. customThe residue thus obtained
  4. washThe aqueous phase was first washed with methylene chloride

Sources & evidence

ORD record
ord-c36dab75d816413984977428bf027e02
Source dataset
uspto-grants-1998_01
Patent number
US05707936

Reaction notes

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