Oxygen → HCID 178483298, compound

HRID 616437Notes

Reaction equation

HRID 616437 reaction equation
[CH3:1][N:2]([CH2:4][C:5](=[CH2:8])[C:6]#[N:7])[CH3:3].[C:9]1([NH:15][NH2:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-]CC.[Na+].O=O.S(=O)(=O)(O)O>C(O)C>[CH3:1][N:2]([CH2:4][CH:5]1[CH2:8][N:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:16][C:6]1=[NH:7])[CH3:3]

Participants

7

Reactant 5

HCID 977OxygenHCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 2723922Sodium ethoxide2×HCID 32597102-Dimethylaminomethylacrylonitrile

Product 1

HCID 178483298HCID 178483298, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Dimethylaminomethylacrylonitrile (11.0g) was added in one portion to a solution of phenylhydrazine (10.8g) and sodium ethoxide (2.3g sodium) in ethanol (100 ml). The product was rapidly oxidised in alkaline solution to a deep purple material; contact with oxygen was prevented by vigorous boiling of the solvent during 11/2 hours reflux. After cooling, the sodium ethoxide was neutralised with sulphuric acid (50 ml 2N) and the mixture was extracted with chloroform (3 × 100 ml). Evaporation of the solvent gave a brown solid (17.8g) which was recrystallised from petroleum ether (boiling point 80°-100° C; 300 ml) to yield colourless plates (16.4g, 75%, melting point 117°-8° C).

Workup

  1. custom2 hours
  2. temperaturereflux
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with chloroform (3 × 100 ml)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cd0c0d02a73d4fb6815c075ced7a489b
Source dataset
uspto-grants-1978_02
Patent number
US04074051

Reaction notes

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