Water → 1-(Diphenylmethyl)imidazolidin-2-one

HRID 1580118Notes

Reaction equation

HRID 1580118 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[CH:13](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CS(C)=O>[C:14]1([CH:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:1]2[CH2:5][CH2:4][NH:3][C:2]2=[O:6])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7035ChlorodiphenylmethaneHCID 84532-ImidazolidinoneHCID 11430Potassium Carbonate

Product 1

HCID 126678101-(Diphenylmethyl)imidazolidin-2-oneYield 43%

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 g (0.25 mole) of K2CO3, 20 g (0.12 mole) of KI and 50.8 g (0.25 mole) of benzhydryl chloride. The reaction mixture was heated with rapid stirring to 100° over 0.3 hr, held at 100° for 1.5 hours and poured into 1.5 l of H2O. The aqueous mixture was extracted with 1.3 l of chloroform. The chloroform extract was washed with 500 ml of H2O, dried over MgSO4 overnight and filtered. The filtrate was concentrated to dryness under reduced pressure leaving 27 g (43%) of a semi-solid. The crude product was washed with 100 ml of ether, air dried and dried at 60° for 2 hours to give 19 g (30%) of a white solid, m.p. 200°-202°. Recrystallization from acetonitrile provided an analytical sample, m.p. 201°-203°.

Workup

  1. temperatureThe reaction mixture was heated
  2. waitheld at 100° for 1.5 hours
  3. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  4. extractionThe chloroform extract
  5. washwas washed with 500 ml of H2O
  6. dry with materialdried over MgSO4 overnight
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5f0cdb0a9b2a456fb722e275f46585d3
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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