Water → 1-(2-Naphthylmethyl)-2-imidazolidinone

HRID 1580119Notes

Reaction equation

HRID 1580119 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1.O>CS(C)=O>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[CH2:14][N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 756322-(Chloromethyl)naphthalene

Product 1

HCID 215651741-(2-Naphthylmethyl)-2-imidazolidinoneYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 21.5g (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 44.3 g (0.25 mole) of 2-(chloromethyl)-naphthalene. The reaction mixture was heated to 105° over 0.3 hours, held at 105°-110° for 1.8 hours and poured with rapid stirring into 1.5 l of 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 to dryness to give 31.5 g (56%) of a light yellow solid, m.p. 102 soften, 120°-138°.

Workup

  1. temperatureThe reaction mixture was heated to 105° over 0.3 hours
  2. additionpoured
  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 to dryness

Sources & evidence

ORD record
ord-0d701499b3dc47d2a697b2d85fffc024
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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