Benzyl Bromide → 4-(2,5-Dioxo 4,4-dimethyl 3-(4-phenylmethoxy-butyl) 1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile

HRID 355595Notes

Reaction equation

HRID 355595 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:28])[C:8](=[O:9])[N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=2)[C:6](=[O:22])[N:5]1[CH2:23][CH2:24][CH2:25][CH2:26][OH:27].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.P(O)(O)([O-])=O.[K+]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:22]=[C:6]1[N:5]([CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:4]([CH3:28])([CH3:3])[C:8](=[O:9])[N:7]1[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:19])([F:20])[F:21])[CH:11]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1329814-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrileHCID 516951Monobasic potassium phosphate

Product 1

HCID 221169094-(2,5-Dioxo 4,4-dimethyl 3-(4-phenylmethoxy-butyl) 1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

48 mg of sodium hydride were added in several lots to 370 mg of the product of Example 58 in solution in 4 ml of dimethylformamide and the mixture was stirred for 30 minutes. Then, 0.12 ml of benzyl bromide and 40 mg of tetrabutylammonium iodide were added and after 90 minutes of reaction, the same amount of each reagent was added. The mixture was stirred for one hour and the reaction medium was poured into an ice-cooled aqueous solution of monopotassium phosphate. Extraction was carried out with ether and the extracts were washed with water and dried. The solvent was eliminated under reduced pressure and the residue was chromatographed on silica (eluant: methylene chloride--acetone 99-1) to obtain 140 mg of the expected product melting at 75°-76° C.

Workup

  1. additionthe same amount of each reagent was added
  2. stirringThe mixture was stirred for one hour
  3. extractionExtraction
  4. washthe extracts were washed with water
  5. customdried
  6. customthe residue was chromatographed on silica (eluant: methylene chloride--acetone 99-1)

Sources & evidence

ORD record
ord-888980a7582d4f20aa82bd95658c2190
Source dataset
uspto-grants-1998_11
Patent number
USRE035956

Reaction notes

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