(3,4-Dichlorophenyl)acetonitrile → HCID 69077483, compound

HRID 388402Notes

Reaction equation

HRID 388402 reaction equation
[NH2:1][C:2]1[S:6][C:5]([CH2:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])=[C:4]([CH3:15])[C:3]=1[C:16]([O:18]CC)=O.[Cl:21][C:22]1[CH:23]=[C:24]([CH2:29][C:30]#[N:31])[CH:25]=[CH:26][C:27]=1[Cl:28]>Cl.O1CCOCC1>[Cl:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:29][C:30]1[NH:31][C:16](=[O:18])[C:3]2[C:4]([CH3:15])=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])[S:6][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 69076944HCID 69076944, compound

Product 1

HCID 69077483HCID 69077483, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A mixture of 900 mg of butyl 5-amino-4-ethoxycarbonyl-3-methyl-2-thiopheneacetate, 558 mg of (3,4-dichlorophenyl)acetonitrile and 20 mL of 4N hydrochloric acid/1,4-dioxane solution was stirred at room temperature overnight. Ice water was added to the reaction mixture, followed by neutralization with 25% aqueous ammonia, extraction with chloroform, drying over anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=50:1) to provide 500 mg (38%) of the title compound.

Workup

  1. extractionfollowed by neutralization with 25% aqueous ammonia, extraction with chloroform
  2. dry with materialdrying over anhydrous magnesium sulfate and removal of the solvent by distillation under reduced pressure
  3. customThe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-342c1c8ec4bd404ba8f9c7df087c5316
Source dataset
uspto-grants-2013_02
Patent number
US08377944B2

Reaction notes

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