Chloroacetonitrile → HCID 19831123, compound

HRID 1493313Notes

Reaction equation

HRID 1493313 reaction equation
[SH:1][CH2:2][C:3]1[NH:4][C:5]([CH3:25])=[C:6]([C:23]#[N:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl[CH2:27][C:28]#[N:29]>CCO>[C:28]([CH2:27][S:1][CH2:2][C:3]1[NH:4][C:5]([CH3:25])=[C:6]([C:23]#[N:24])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])#[N:29]

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 19831124HCID 19831124, compound

Product 1

HCID 19831123HCID 19831123, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-mercaptomethyl-3-carboethoxy-5-cyano-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (3 g), 2-chloroacetonitrile (1 g) and 1,4-diazabicyclo-2,2,2-octa ne (0.8 g) in EtOH (30 ml) is heated at reflux temperature for six hours. Then the reaction is cooled to room temperature and after usual work-up and purification by columnchromatography (SiO2 90 g; eluent Et2O/AcOEt 90/10) gives 1.8 g of 2-(cyanomethylthio)methyl-3-carboethoxy-5-cyano-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine.

Workup

  1. temperatureat reflux temperature for six hours
  2. customafter usual work-up and purification by columnchromatography (SiO2 90 g; eluent Et2O/AcOEt 90/10)

Sources & evidence

ORD record
ord-211933948542444a93bf4b220b5167f5
Source dataset
uspto-grants-1991_06
Patent number
US05021436

Reaction notes

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