Chloroacetonitrile → 2-(3-Methoxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride

HRID 622419Notes

Reaction equation

HRID 622419 reaction equation
[Cl:1][CH2:2][C:3]#[N:4].[Na].Cl.[CH3:7][O:8][N:9]=[C:10]1[CH2:14][CH2:13][NH:12][CH2:11]1>CO>[ClH:1].[CH3:7][O:8][N:9]=[C:10]1[CH2:14][CH2:13][N:12]([C:3](=[NH:4])[CH2:2][Cl:1])[CH2:11]1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 867424283-Methoxyiminopyrrolidine hydrochloride

Product 1

HCID 867424272-(3-Methoxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.63 ml of chloroacetonitrile was added to a solution of 23 mg of metallic sodium in 4 ml of absolute methanol, the mixture was stirred at room temperature for about 30 minutes, then 1.5 g of 3-methoxyiminopyrrolidine hydrochloride were added and the resulting mixture stirred for a further 2 hours. After completion of the reaction, the solvent was distilled off and the concentrate mixed with anhydrous ether. The crystals which separated out were collected by filtration and washed with ether, giving 2.2 g of 2-(3-methoxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride.

Workup

  1. stirringthe resulting mixture stirred for a further 2 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionthe concentrate mixed with anhydrous ether
  5. customThe crystals which separated out
  6. filtrationwere collected by filtration
  7. washwashed with ether

Sources & evidence

ORD record
ord-756d2cb4878d46e4a6c00d0a0fdbe11e
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

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