Sodium hydride → HCID 69036645, compound

HRID 1453812Notes

Reaction equation

HRID 1453812 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([NH2:13])=[O:12].[CH2:16]([N:23]=[C:24]=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[CH2:27][C:28](OC)=[O:29]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:16]([N:23]1[C:28](=[O:29])[CH2:27][N:13]([C:11]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[C:4]([F:3])([F:14])[F:15])=[O:12])[C:24]1=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 76639Benzyl isocyanateHCID 27826434-Trifluoromethylnicotinamide

Product 1

HCID 69036645HCID 69036645, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.090 g, 60% dispersion in mineral oil) was added to a solution of 4-trifluoromethyl-3-pyridinecarboxamide (0.40 g) in N,N-dimethylformamide at 20° C., and stirred for 1 hour. Benzyl isocyanate (0.31 ml) was added and the mixture stirred at 20° C. for 2 hours, then methyl bromoacetate (0.30 ml) added and stirring continued for 5 hours. Ethyl acetate and water were added to the solution and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on silica gel, eluting with n-hexane/ethyl acetate (2:1), to give 3-benzyl-1-(4-trifluoromethyl-3-pyridylcarbonyl)hydantoin (0.50 g, Compound S-132).

Workup

  1. stirringthe mixture stirred at 20° C. for 2 hours
  2. stirringstirring
  3. waitcontinued for 5 hours
  4. dry with materialthe organic phase dried (magnesium sulfate)
  5. customevaporated
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-107e391d15284a03b3c6de9f1c2bb296
Source dataset
uspto-grants-2009_01
Patent number
US07476685B2

Reaction notes

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