Aniline → HCID 178510456, compound

HRID 359938Notes

Reaction equation

HRID 359938 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].C(N(CCCC)CCCC)CCC.Cl[CH2:20][C:21](Cl)=[O:22].[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.O>[NH2:4][C:3]1[N:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][C:21](=[O:22])[C:2]=1[C:1]#[N:5]

Participants

7

Reactant 4

HCID 6115AnilineHCID 6577Chloroacetyl chlorideHCID 7622TributylamineHCID 8010Malononitrile

Product 1

HCID 178510456HCID 178510456, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

26.4 g of malononitrile were dissolved in 150 ml of DMF and cooled to 0° C. While cooling, 148 g of tributylamine and 45 g of chloracetyl chloride were simultaneously added dropwise to this, and the mixture was stirred at room temperature for 30 minutes. 42 g of aniline were then added to the mixture, which was stirred at 80° C. for 15 hours and then 200 g of water were added. After cooling to room temperature, the organic phase was separated off and digested with dichloromethane. The precipitate was filtered off with suction, washed and dried. 37.4 g (46% of theory) of the compound of the formula ##STR28## of melting point 285° to 290° C. were obtained. The IR, NMR, UV and mass spectra and the elemental analysis are consistent with the structural formula

Workup

  1. temperatureWhile cooling
  2. stirringwas stirred at 80° C. for 15 hours
  3. temperatureAfter cooling to room temperature
  4. customthe organic phase was separated off
  5. filtrationThe precipitate was filtered off with suction
  6. washwashed
  7. customdried
  8. custom37.4 g (46% of theory) of the compound of the formula ##STR28## of melting point 285° to 290° C. were obtained

Sources & evidence

ORD record
ord-3ef26cffcfea4deeb641b54c0b090f38
Source dataset
uspto-grants-1991_03
Patent number
US05003081

Reaction notes

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