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

HRID 355585

반응식

HRID 355585 반응식
[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]

참가 물질

5

반응물 3

HCID 4493NilutamideHCID 6328Methyl iodideHCID 24758Sodium hydride

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A solution of 3.17 g of 1-(3-trifluoromethyl-4-nitrophenyl)-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.

후처리

  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

출처 및 근거

ORD 기록
ord-9a76763136c5491d9a191dde16b2e7d5
출처 데이터셋
uspto-grants-1998_11
특허 번호
USRE035956

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