Water → HCID 46947722, compound

HRID 2370582Notes

Reaction equation

HRID 2370582 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].CS(O[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][S:39][CH2:40][CH2:41][CH2:42][C:43]([F:49])([F:48])[C:44]([F:47])([F:46])[F:45])(=O)=O.O>CN(C=O)C>[CH3:3][C:4]1([CH3:24])[N:8]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][S:39][CH2:40][CH2:41][CH2:42][C:43]([F:49])([F:48])[C:44]([F:45])([F:46])[F:47])[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]

Participants

6

Reactant 4

HCID 962WaterHCID 4493NilutamideHCID 24758Sodium hydrideHCID 58899364HCID 58899364, compound

Product 1

HCID 46947722HCID 46947722, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

NaH (at 60%) (44 mg, 1.1 mmole), is added under argon to a solution of 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]-imidazolidine-2,4-dione (317 mg, 1 mmole) in anhydrous DMF (8 ml). A release of gas accompanies the change in colour of the reaction medium which becomes orange. Stirring is maintained for 1 hour at 23° C. before adding 9-[(4,4,5,5,5-pentafluoropentyl)-thio]nonyl methanesulphonate (prepared according to an experimental protocol described in WO 2005077968) (332 mg, 0.8 mmole). After reaction for 15 hours, the reaction medium is poured into water (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: CH2Cl2/AcOEt: 1/1 to 0/1). The expected compound is obtained in the form of a pale yellow oil with a yield of 72% (364 mg).

Workup

  1. customprepared
  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: CH2Cl2/AcOEt: 1/1 to 0/1)

Sources & evidence

ORD record
ord-e5ffe973a6024e05b6374353fd9d110c
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

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