Water → 4-[4,4-Dimethyl 2,5-dioxo 3-(4-methoxybutyl) 1-imidazolidinyl] 2-(trifluoromethyl)-benzonitrile

HRID 355596Notes

Reaction equation

HRID 355596 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].[CH3:29]I.O>CN(C)C=O>[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:19])([F:20])[F:21])[CH:11]=2)[C:6](=[O:22])[N:5]1[CH2:23][CH2:24][CH2:25][CH2:26][O:27][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 1329814-(3-(4-Hydroxybutyl)-4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile

Product 1

HCID 221169174-[4,4-Dimethyl 2,5-dioxo 3-(4-methoxybutyl) 1-imidazolidinyl] 2-(trifluoromethyl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of sodium hydride were added in several lots to 370 mg of the product of Example 58 in solution in 3 ml of dimethylformamide and the mixture was stirred for 20 minutes. 0.06 ml of methyl iodide were added and the mixture was stirred for one hour. A further 50 mg of sodium hydride were added and then after 20 minutes, 0.06 ml of methyl iodide were added. The reaction medium was poured into water and extracted with ether. The extracts were washed with water, dried and the solvent was evaporated. The residue was chromatographed on silica (eluant: methylene chloride--acetone 98-2) to obtain 135 mg of the expected product melting at 80°-81° C.

Workup

  1. stirringthe mixture was stirred for one hour
  2. waitafter 20 minutes
  3. extractionextracted with ether
  4. washThe extracts were washed with water
  5. customdried
  6. customthe solvent was evaporated
  7. customThe residue was chromatographed on silica (eluant: methylene chloride--acetone 98-2)

Sources & evidence

ORD record
ord-c4190a384c3544f4a17c014e74f707bf
Source dataset
uspto-grants-1998_11
Patent number
USRE035956

Reaction notes

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