Ethyl propiolate → HCID 136035283, compound

HRID 1112717Notes

Reaction equation

HRID 1112717 reaction equation
[N+:1](=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][C:4]1=[O:13])=[N-:2].[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[C:15]#[CH:16]>C1(C)C(C)=CC=CC=1>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]2[NH:5][C:4](=[O:13])[N:1]3[N:2]=[C:15]([C:14]([O:18][CH2:19][CH3:20])=[O:17])[CH:16]=[C:3]3[C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 178514323HCID 178514323, compound

Product 1

HCID 136035283HCID 136035283, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Seven and one-half g (0.039 mole) of 3-diazo-5-chloro-oxindole and 8.4 g (0.086 mole) of ethyl propiolate are dissolved in 400 ml of xylene and heated to reflux (under nitrogen) for 1.5 hours, during which time a copious amount of solid forms. The reaction mixture is cooled to room temperature, filtered, washed with ether and dried to give 10 g (88% yield) of TLC pure material. This is crystallized from chloroform/methanol (4:1) and then from methanol to give 8.1 g of analytically pure compound.

Workup

  1. temperatureheated
  2. temperatureto reflux (under nitrogen) for 1.5 hours
  3. filtrationfiltered
  4. washwashed with ether
  5. customdried
  6. customto give 10 g (88% yield) of TLC pure material
  7. customThis is crystallized from chloroform/methanol (4:1)
  8. customfrom methanol to give 8.1 g of analytically pure compound

Sources & evidence

ORD record
ord-246f7b08994f431b84417cf555513b27
Source dataset
uspto-grants-1978_10
Patent number
US04123532

Reaction notes

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