Water → HCID 23301864, compound

HRID 1580127Notes

Reaction equation

HRID 1580127 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].[NH:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22].O>CS(C)=O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:17]2[CH2:21][CH2:20][NH:19][C:18]2=[O:22])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 23301864HCID 23301864, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 20.95 g (0.107 mole) of 4-cyanobenzyl bromide, 14.7 g (0.107 mole) K2CO3, 5.0 g KI, and 10.32 g (0.12 mole) 2-imidazolidinone in 125 ml dimethylsulfoxide was stirred at 100°-110° for 30 minutes, cooled, and poured into 400 ml cold tap water. The mixture was stirred at room temperature for 30 minutes and extracted with 250 ml chloroform. The chloroform extract was washed with 3 × 250 ml H2O, dried (MgSO4), and concentrated to dryness in vacuo to give an oily residue. Crystallization from 60 ml toluene gave 5.50 g of the crude product. Further recrystallization from toluene gave 4.34 g (20%) of the nitrile, m.p. 127°-133°. The analytical sample, m.p. 134°-136°, was obtained by recrystallization from toluene.

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. extractionextracted with 250 ml chloroform
  4. extractionThe chloroform extract
  5. washwas washed with 3 × 250 ml H2O
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to dryness in vacuo
  8. customto give an oily residue
  9. customCrystallization from 60 ml toluene
  10. customgave 5.50 g of the crude product
  11. customFurther recrystallization from toluene

Sources & evidence

ORD record
ord-c6956e8853ba4fbf98df29ae229fa4ff
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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