Water → HCID 3244179, compound

HRID 1580121Notes

Reaction equation

HRID 1580121 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C([O-])([O-])=O.[K+].[K+].[F:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl.O>CS(C)=O>[F:13][C:14]1[CH:21]=[CH:20][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 84532-ImidazolidinoneHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 11430Potassium Carbonate

Product 1

HCID 3244179HCID 3244179, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 21.5 g (0.25 mole) portion of 2-imidazolidinone in 125 ml of dimethylsulfoxide was treated with 34.5 g (0.25 mole) of K2CO3, 20 g (0.12 mole) of KI and 36.3 g (0.25 mole) of 2-fluorobenzyl chloride. The reaction mixture was heated to 105° over 0.3 hours, held at 105° for 1.8 hours, and poured into 1.51 of water all with rapid stirring. 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 under reduced pressure to give 42 g (86%) of a light yellow oil. The crude product was washed with 100 ml of ether to give 10 g (20%) of a white solid m.p. 72°-76°.

Workup

  1. temperatureThe reaction mixture was heated to 105° over 0.3 hours
  2. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  3. extractionThe chloroform extract
  4. washwas washed with 500 ml of H2O
  5. dry with materialdried over MgSO4 overnight
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d67840d2f22640afbcffc31ccc2d2368
Source dataset
uspto-grants-1976_01
Patent number
US03932452

Reaction notes

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