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

HRID 2107765Notes

Reaction equation

HRID 2107765 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-4dc79ba0711f45b38502f371a38a8224
Source dataset
uspto-grants-1990_06
Patent number
US04935437

Reaction notes

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