Ethyl propiolate → HCID 131711223, compound

HRID 1763462Notes

Reaction equation

HRID 1763462 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[N+:13]=[N-:14].[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[C:16]#[CH:17]>C1C=CC=CC=1>[CH2:20]([O:19][C:15](=[O:18])[CH:16]=[CH:17][N:8]1[C:9]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[C:6]2=[CH:17][C:16]([C:15]([O:19][CH2:20][CH3:21])=[O:18])=[N:14][N:13]2[C:7]1=[O:12])[CH3:21]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 178487250HCID 178487250, compound

Product 1

HCID 131711223HCID 131711223, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1.5 g (0.0079 mole) of 5-methoxy-3-diazooxindole and 0.99 g (0.01 mole of 1.3 equiv.) of 99% ethyl propiolate are refluxed in benzene (50 ml) under N2 for 24 hours. The reaction mixture is cooled down to room temperature and the precipitates that form are filtered off and washed well with ether, dried in a vacuum oven at 60° for 2 hours. Yield: 661.8 mg, m.p. 202°-204°, Rf 0.3. This crude product is taken up in 75 ml of absolute ethanol, treated with activated carbon, filtered through a celite pad and the clear filtrate is concentrated down to a volume of ~50 ml on the steam bath. After cooling, the precipitates that form are filtered off. The product is dried overnight in a vacuum oven at room temperature. Yield: 555.4 mg, m.p. 225°-227°.

Workup

  1. customthe precipitates that form
  2. filtrationare filtered off
  3. washwashed well with ether
  4. customdried in a vacuum oven at 60° for 2 hours
  5. additiontreated with activated carbon
  6. filtrationfiltered through a celite pad
  7. concentrationthe clear filtrate is concentrated down to a volume of ~50 ml on the steam bath
  8. temperatureAfter cooling
  9. customthe precipitates that form
  10. filtrationare filtered off
  11. customThe product is dried overnight in a vacuum oven at room temperature

Sources & evidence

ORD record
ord-3217b355dc424b1fa1fef591a2f4f2b6
Source dataset
uspto-grants-1978_09
Patent number
US04112098

Reaction notes

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