Ethylamine → HCID 178462792, compound

HRID 359933Notes

Reaction equation

HRID 359933 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6]([N:8](CC)[CH2:9][CH3:10])[CH3:7].ClCC(Cl)=[O:16].C(N)C>CN(C=O)C>[NH2:4][C:3]1[N:8]([CH2:9][CH3:10])[CH2:6][C:7](=[O:16])[C:2]=1[C:1]#[N:5]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 6577Chloroacetyl chlorideHCID 8010MalononitrileHCID 8471Triethylamine

Product 1

HCID 178462792HCID 178462792, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

19.8 g of malononitrile were dissolved in 30 ml of DMF and cooled to 0° C. While cooling, 61 g of triethylamine and 32 g of chloroacetyl chloride were simultaneously added dropwise to this, and the mixture was then stirred at 10° C. for 10 minutes. Subsequently, while cooling, 49 g of 70% by weight aqueous ethylamine solution were added dropwise, and the mixture was stirred at room temperature for 8 hours. The precipitate was filtered off with suction, washed and dried at 50° C. 41.8 g (92%) of impure crude product were obtained and were recrystallized from 1:1 isopropanol/water with the addition of active carbon. This resulted in 10.9 g (24% of theory) of the compound of the formula ##STR23## of melting point 278° to 280° C. The IR, NMR, UV and mass spectra and the elemental analysis are consistent with the structural formula.

Workup

  1. temperatureWhile cooling
  2. temperatureSubsequently, while cooling
  3. stirringthe mixture was stirred at room temperature for 8 hours
  4. filtrationThe precipitate was filtered off with suction
  5. washwashed
  6. customdried at 50° C

Sources & evidence

ORD record
ord-063cb2d1013143d7b1127d42980e9336
Source dataset
uspto-grants-1991_03
Patent number
US05003081

Reaction notes

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