Nilutamide → 1-(4-Nitro-3-trifluoromethyl-phenyl)-3,4,4-trimethyl-2,5-imidazolidinedione

HRID 35937

反応式

HRID 35937 の反応式
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[NH:14][C:13]2=[O:20])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:25]I>CN(C)C=O>[N+:9]([C:8]1[CH:7]=[CH:6][C:5]([N:12]2[C:16](=[O:17])[C:15]([CH3:19])([CH3:18])[N:14]([CH3:25])[C:13]2=[O:20])=[CH:4][C:3]=1[C:2]([F:1])([F:21])[F:22])([O-:11])=[O:10]

参加物

5

反応物 3

HCID 4493NilutamideHCID 6328Methyl iodideHCID 24758Sodium hydride

生成物 1

HCID 221169221-(4-Nitro-3-trifluoromethyl-phenyl)-3,4,4-trimethyl-2,5-imidazolidinedione

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 3.17 g of 1-(3-trifluoromethyl-4-nitro-phenyl)-4,4-dimethyl-imidazoline-2,5-dione (French Patent No. 2,329,276) and 32 ml of dimethylformamide were added at 23° C. to 26° C. to a 50% suspension of 492 mg of sodium hydride in oil and 3 ml of dimethylformamide and after stirring for 15 minutes, a solution of 0.7 ml of methyl iodide in 2 ml of dimethylformamide was added. The mixture was stirred for 25 minutes at 24° C. to 28° C. and was then poured into 200 g of a 1--1 water-ice mixture. The mixture was extracted with ether and the organic phase was washed with saturated aqueous sodium chloride, dried, filtered and evaporated to dryness under reduced pressure to obtain 3.6 g of the desired product melting at 116° C. An analytical sample was crystallized from isopropyl alcohol to obtain 2.73 g of the product melting at 116° C.

後処理

  1. stirringThe mixture was stirred for 25 minutes at 24° C. to 28° C.
  2. extractionThe mixture was extracted with ether
  3. washthe organic phase was washed with saturated aqueous sodium chloride
  4. customdried
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-e4df9f5c88c042ed901ecdcce32dcd67
出典データセット
uspto-grants-1995_05
特許番号
US05411981

関連ノート

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