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

HRID 622422Notes

Reaction equation

HRID 622422 reaction equation
[Cl:1][CH2:2][C:3]#[N:4].C[O-].[Na+].[Na].Cl.[OH:10][N:11]=[C:12]1[CH2:16][CH2:15][NH:14][CH2:13]1>CO>[ClH:1].[OH:10][N:11]=[C:12]1[CH2:16][CH2:15][N:14]([C:3](=[NH:4])[CH2:2][Cl:1])[CH2:13]1

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 867424323-Hydroxyiminopyrrolidine hydrochloride

Product 1

HCID 867424302-(3-Hydroxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.44 ml of chloroacetonitrile was added to a solution of sodium methoxide, prepared by dissolving 16 mg of metallic sodium in 2.8 ml of absolute methanol, and the mixture was stirred at room temperature for about 30 minutes. 950 mg of 3-hydroxyiminopyrrolidine hydrochloride were then added, and the mixture was stirred for a further 2 hours. After completion of the reaction, the solvent was distilled off and the concentrate mixed with anhydrous ether, giving a crystalline product. The crystals were collected by filtration and washed with ether, giving 1.15 g of 2-(3-hydroxyiminopyrrolidin-1-yl)-2-iminoethylchloride hydrochloride.

Workup

  1. customprepared
  2. stirringthe mixture was stirred for a further 2 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off
  5. additionthe concentrate mixed with anhydrous ether
  6. customgiving a crystalline product
  7. filtrationThe crystals were collected by filtration
  8. washwashed with ether

Sources & evidence

ORD record
ord-abb79e319b9644a78ad6643fbb1f1505
Source dataset
uspto-grants-1988_09
Patent number
US04771046

Reaction notes

Loading…