Water → 1-{[4-(Benzyloxy)phenyl]methyl}imidazolidin-2-one

HRID 1580126Notes

Reaction equation

HRID 1580126 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CS(C)=O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:1]2[CH2:5][CH2:4][NH:3][C:2]2=[O:6])=[CH:27][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 700424-Benzyloxybenzyl chloride

Product 1

HCID 215651681-{[4-(Benzyloxy)phenyl]methyl}imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 21.5 g (0.25 mole) portion of 2-imidazolidinone in 250 ml of dimethylsulfoxide was treated with 34.5 (0.25 mole) of K2CO3, 20.0 g (0.12 mole) of KI and 58.5 g (0.25 mole) of 4-benzyloxybenzyl chloride. The reaction mixture was heated to 105° over 0.5 hours, held at 105°-110° for 1.7 hours, poured with stirring into 1.5 l of H2O, stirred for 0.3 hours and filtered. The green-yellow solid was washed with 300 ml of H2O, air dried overnight, and dried to a constant weight at 60°, m.p. 110°-122°. Yield: 62 g (87%). Recrystallization from 1:1 methane: water gave an analytical sample, m.p. 156°-157°.

Workup

  1. temperatureThe reaction mixture was heated to 105° over 0.5 hours
  2. additionpoured
  3. filtrationfiltered
  4. washThe green-yellow solid was washed with 300 ml of H2O, air
  5. customdried overnight
  6. customdried to a constant weight at 60°
  7. customRecrystallization from 1:1 methane
  8. customwater gave an analytical sample, m.p. 156°-157°

Sources & evidence

ORD record
ord-9cb641881398409d93cf0b77a907d537
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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