Water → 1-[(4-Bromophenyl)methyl]-2-imidazolidinone

HRID 1580122Notes

Reaction equation

HRID 1580122 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.O>CS(C)=O>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:1]2[CH2:5][CH2:4][NH:3][C:2]2=[O:6])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromide

Product 1

HCID 215651691-[(4-Bromophenyl)methyl]-2-imidazolidinoneYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 12.4 g (0.14 mole) portion of 2-imidazolidinone in 125 ml of dimethylsulfoxide treated with 19.9 g (0.14 mole) of K2CO3, 11.5 g (0.069 mole) of KI and 36.0 g (0.14 mole) of 4-bromobenzylbromide. The reaction mixture was heated to 105° over 0.3 hours, held at 105° with stirring for 1.8 hours, and poured into 1.51 of cold water. The aqueous mixture was extracted with 1.3 l of chloroform. The chloroform extract was washed with 500 ml of water, dried over MgSO4 overnight and filtered. The filtrate was concentrated under reduced pressure to give 36 g (100%) of a light yellow semisolid. The crude product was crystallized using 150 ml of ether, filtered, air dried and dried at 60° for 4 hours to give 15 (42%) of a white solid m.p. 163°-167°. Recrystallization from acetonitrile gave an analytical sample, m.p. 166°-168°.

Workup

  1. temperatureThe reaction mixture was heated to 105° over 0.3 hours
  2. customheld at 105°
  3. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  4. extractionThe chloroform extract
  5. washwas washed with 500 ml of water
  6. dry with materialdried over MgSO4 overnight
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9380dde7fbfe4573a8de5baa399f752d
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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