Chloroacetonitrile → HCID 14369600, compound

HRID 1200096Notes

Reaction equation

HRID 1200096 reaction equation
Cl[CH2:2][C:3]#[N:4].P(OCC)(OCC)OCC.C[O-].[Na+].[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:29]([CH:30]=O)=[CH:28][NH:27][CH:26]=1>CN(C)C=O.O>[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:29](/[CH:30]=[CH:2]\[C:3]#[N:4])=[CH:28][NH:27][CH:26]=1.[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:29](/[CH:30]=[CH:2]/[C:3]#[N:4])=[CH:28][NH:27][CH:26]=1

Participants

8

Reactant 4

HCID 7856ChloroacetonitrileHCID 31215Triethyl phosphiteHCID 10942334Sodium MethoxideHCID 19864626HCID 19864626, compound

Product 2

HCID 14369600HCID 14369600, compoundYield 36%HCID 14369601HCID 14369601, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2.5 g (0.0326 mol) of chloroacetonitrile and 5.4 g (0.0326 mol) of triethyl phosphite are heated to 200° C. until the evolution of gas has ended. 30 ml of dimethylformamide and 1.8 g (0.034 mol) of sodium methylate are added to the cooled mixture and 3.0 g (0.0162 mol) of 3-(2-methylphenyl)-pyrrole-4-aldehyde in 5 ml of dimethylformamide are then added dropwise at 0° C. with stirring. After completion of the addition, the reaction mixture is stirred for 16 hours at room temperature and then added to water, the mixture is extracted with ethyl acetate, washed using water, dried over sodium sulphate and concentrated in vacuo, and the residue is purified by chromatography on silica gel (eluant ethyl acetate/cyclohexane 5 : 1). 0.5 g (15% of theory) of (Z)-β-[3-(2-methylphenyl)pyrrol -4-yl]-acrylonitrile of melting point 74° C.-75° C. and 1.2 g (36% of theory) of (E)-β-[3-(2-methylphenyl)pyrrol -4-yl]-acrylonitrile of melting point 152° C.-154° C. are obtained.

Workup

  1. additionare then added dropwise at 0° C.
  2. additionAfter completion of the addition
  3. stirringthe reaction mixture is stirred for 16 hours at room temperature
  4. extractionthe mixture is extracted with ethyl acetate
  5. washwashed
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customthe residue is purified by chromatography on silica gel (eluant ethyl acetate/cyclohexane 5 : 1)

Sources & evidence

ORD record
ord-5a4073e91d2f43b2b842fcf753e185e1
Source dataset
uspto-grants-1990_02
Patent number
US04904687

Reaction notes

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