Methylamine → HCID 178481140, compound

HRID 359932Notes

Reaction equation

HRID 359932 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6]([N:10]([CH2:15]CCC)CCCC)[CH2:7]CC.ClCC(Cl)=[O:22].CN>CN(C)C=O>[NH2:4][C:3]1[N:10]([CH3:15])[CH2:6][C:7](=[O:22])[C:2]=1[C:1]#[N:5]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 6577Chloroacetyl chlorideHCID 7622TributylamineHCID 8010Malononitrile

Product 1

HCID 178481140HCID 178481140, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

99 g of malononitrile were dissolved in 150 ml of N,N-dimethylformamide (DMF) and cooled to 0° C. While cooling, 556 g of tributylamine and 169.5 g of chloroacetyl chloride were simultaneously added dropwise to this, and the mixture was then stirred at 10° C. for 10 minutes. The reaction mixture was subsequently added to a mixture of 1.5 kg of ice and 327 ml of 40% by weight aqueous methylamine solution and stirred at room temperature for 8 hours. The precipitate was filtered off with suction, washed and dried in an oven at 50° C. 124 g (60% of theory) of the compound of the formula ##STR22## of melting point 300° 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. stirringstirred at room temperature for 8 hours
  3. filtrationThe precipitate was filtered off with suction
  4. washwashed
  5. customdried in an oven at 50° C
  6. custom124 g (60% of theory) of the compound of the formula ##STR22## of melting point 300° C. were obtained

Sources & evidence

ORD record
ord-a6e503c8ac3e49be8506da80e2a0f8ae
Source dataset
uspto-grants-1991_03
Patent number
US05003081

Reaction notes

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