Water → HCID 21565176, compound

HRID 1580124Notes

Reaction equation

HRID 1580124 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[CH2:16]Cl.O>CS(C)=O>[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[CH2:16][N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 84532-ImidazolidinoneHCID 11430Potassium Carbonate

Product 1

HCID 21565176HCID 21565176, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 21.5 g (0.25 mole) portion of 2-imidazolidinone in 200 ml of dimethylsulfoxide was treated with 34.5 g (0.25 mole) of K2CO3, 20 g (0.12 mole) of KI and 48.9 g (0.25 mole) of 2,4-dichlorobenzyl chloride. The reaction mixture was heated with stirring to 105° over 0.3 hours, held at 105° 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 580 ml of water, dried over MgSO4 overnight and filtered. The filtrate was concentrated under reduced pressure leaving 47 g (77%) of a light yellow oil. The oil was crystallized with 125 ml of ether, filtered, air dried, and dried to a constant weight at 60° to give 19 g (31%) of a white solid, m.p. 116°-118°.

Workup

  1. temperatureThe reaction mixture was heated
  2. waitheld at 105° for 1.8 hours
  3. additionpoured
  4. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  5. extractionThe chloroform extract
  6. washwas washed with 580 ml of water
  7. dry with materialdried over MgSO4 overnight
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d303e6cb5d44186afacac6a596ff815
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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