Nilutamide → HCID 46945768, compound

HRID 2370584Notes

Reaction equation

HRID 2370584 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:24])[NH:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=2)[C:5]1=[O:23].[I:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]I.[NH4+].[Cl-]>CN(C=O)C>[I:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:8]1[C:4]([CH3:24])([CH3:3])[C:5](=[O:23])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=2)[C:7]1=[O:9]

Participants

6

Reactant 4

HCID 4493NilutamideHCID 123541,5-DiiodopentaneHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 46945768HCID 46945768, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

NaH (to 60%) (65 mg, 1.6 mmole) is added under argon to a solution of 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-imidazolidine-2,4-dione (500 mg, 1.6 mmole) in anhydrous DMF (20 ml). A gaseous release accompanies the change of colour of the reaction medium which becomes orange. The stirring is maintained for 1 hour at 23° C. before adding, without dilution, the 1,5-diiodopentane (350 μl, 2.4 mmoles). After reaction for 15 hours, the reaction medium is poured into a saturated aqueous solution of NH4Cl (25 ml) and extracted with AcOEt (2×25 ml). The organic phases are combined and washed successively with water (25 ml) and salt water (25 ml). After drying over Na2SO4, the organic solution is filtered and concentrated under vacuum. The evaporation residue is purified on a silica column (eluent: Heptane/AcOEt:7/3 to 6/4). The expected compound is obtained in the form of a colourless oil with a yield of 47% (380 mg).

Workup

  1. additionbefore adding, without dilution
  2. customAfter reaction for 15 hours
  3. extractionextracted with AcOEt (2×25 ml)
  4. washwashed successively with water (25 ml) and salt water (25 ml)
  5. dry with materialAfter drying over Na2SO4
  6. filtrationthe organic solution is filtered
  7. concentrationconcentrated under vacuum
  8. customThe evaporation residue is purified on a silica column (eluent: Heptane/AcOEt:7/3 to 6/4)

Sources & evidence

ORD record
ord-4f4f974cb908456da9fd0e22f3f9585e
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

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