Pyridine → 2-(3-(Chloromethyl)-5-(2-cyanopropan-2-yl)phenyl)-2-methylpropanenitrile

HRID 1636803Notes

Reaction equation

HRID 1636803 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=1.N1C=CC=CC=1.S(Cl)([Cl:27])=O>ClCCl>[Cl:27][CH2:2][C:3]1[CH:4]=[C:5]([C:14]([CH3:18])([CH3:17])[C:15]#[N:16])[CH:6]=[C:7]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 193493981,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-

Product 1

HCID 193493842-(3-(Chloromethyl)-5-(2-cyanopropan-2-yl)phenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2'-(5-hydroxymethyl-1,3-phenylene)di-(2-methylpropiononitrile), (3.8 g) and pyridine (1.58 g) in dichloromethane (10 ml) was stirred, and cooled in an ice bath, while thionyl chloride (3 g) was added over 10 minutes. The solution was kept at room temperature for 2 h and then heated under reflux for 1 h and evaporated to dryness under reduced pressure The residue was partitioned between water and ethyl acetate and the organic phase was separated, dried and evaporated to dryness under reduced pressure to give 2,2'-(5-chloromethyl-1,3-phenylene)di(2-methylpropiononitrile), which was used without further purification.

Workup

  1. additionwas added over 10 minutes
  2. temperatureheated
  3. temperatureunder reflux for 1 h
  4. customevaporated to dryness under reduced pressure The residue
  5. customwas partitioned between water and ethyl acetate
  6. customthe organic phase was separated
  7. customdried
  8. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-59bbcfffe7ec4d61b604b6bb29415ee1
Source dataset
uspto-grants-2000_03
Patent number
USRE036617

Reaction notes

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