Malononitrile → HCID 54446985, compound

HRID 616497Notes

Reaction equation

HRID 616497 reaction equation
C(N(CC)CC)C.[C:8](#[N:12])[CH2:9][C:10]#[N:11].[Cl-].Cl[C:15]([Cl:21])=[N+:16]([CH2:19][CH3:20])[CH2:17][CH3:18]>ClC1C=CC=CC=1>[Cl:21][C:15]([N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[C:9]([C:8]#[N:12])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 12331502Dichloro-N,N-diethylmethaniminium chloride

Product 1

HCID 54446985HCID 54446985, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

A solution of 12.1 g of triethylamine, 4.0 g of malononitrile, and 20 ml of chlorobenzene was added to a slurry of 11.4 g of N-(dichloromethylene)-N,N-diethylammonium chloride and 50 ml of chlorobenzene, at ambient temperature. The reaction temperature was kept below 50° by controlling the rate of addition (time required for complete addition, 30 minutes). After addition, the reaction mixture was stirred for four hours while it returned to ambient temperature. The reaction mixture was filtered and the filtrate concentrated on the rotary evaporator to give a brownish-red liquid. Vacuum distillation gave 3.7 g of liquid 3-chloro-2-cyano-3-(diethylamino)propenenitrile; b.p. 127°-131°/0.05 mm Hg. The ir and nmr spectra were consistent with the assigned structure.

Workup

  1. customwas kept below 50°
  2. additionthe rate of addition (time required for complete addition, 30 minutes)
  3. additionAfter addition
  4. customreturned to ambient temperature
  5. filtrationThe reaction mixture was filtered
  6. concentrationthe filtrate concentrated on the rotary evaporator
  7. customto give a brownish-red liquid
  8. distillationVacuum distillation

Sources & evidence

ORD record
ord-f5cc1e970d8f47a9b4e12466066e45f1
Source dataset
uspto-grants-1978_02
Patent number
US04075001

Reaction notes

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