Chloroacetyl chloride → HCID 20064396, compound

HRID 359937Notes

Reaction equation

HRID 359937 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH2:6]([N:8](CC)CC)C.Cl[CH2:14][C:15](Cl)=[O:16].[CH3:18][O:19][CH2:20][CH2:21]N>CN(C=O)C>[C:6]([C:3]1[N:4]([CH2:21][CH2:20][O:19][CH3:18])[CH2:14][C:15](=[O:16])[C:2]=1[C:1]#[N:5])#[N:8]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8010MalononitrileHCID 80182-MethoxyethylamineHCID 8471Triethylamine

Product 1

HCID 20064396HCID 20064396, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

99 g of malononitrile were dissolved in 150 ml of DMF and cooled to 0° C. While cooling, 306 g of triethylamine and 159 g of chloracetyl chloride were simultaneously added dropwise to this, and the mixture was stirred at 10° C. for 10 minutes. The mixture was then added to a mixture of 1.5 kg of ice and 291 g of 2-methoxyethylamine and stirred at room temperature for 8 hours. The volatiles were removed by distillation at 100° C. under atmospheric pressure, and the distillation residue was concentrated in a rotary evaporator at the water pump. The residue was recrystallized from 500 ml of isopropanol. The precipitate was filtered off with suction, washed and dried at 50° C. 205.5 g (76% of theory) of the compound of the formula ##STR27## of melting point 108° to 110° 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. customThe volatiles were removed by distillation at 100° C. under atmospheric pressure
  4. concentrationthe distillation residue was concentrated in a rotary evaporator at the water pump
  5. customThe residue was recrystallized from 500 ml of isopropanol
  6. filtrationThe precipitate was filtered off with suction
  7. washwashed
  8. customdried at 50° C
  9. custom205.5 g (76% of theory) of the compound of the formula ##STR27## of melting point 108° to 110° C. were obtained

Sources & evidence

ORD record
ord-f029af3700f64f4ab45fe417b9abd60f
Source dataset
uspto-grants-1991_03
Patent number
US05003081

Reaction notes

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