Stannous chloride dihydrate → 3-[2-(4-Amino-phenyl)-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one

HRID 507402

반응식

HRID 507402 반응식
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:5](=[O:18])[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1.O.O.Cl[Sn]Cl>C(O)C.O.N>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][N:6]2[C:5](=[O:18])[C:4]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:3]=[C:2]2[CH3:1])=[CH:14][CH:13]=1

참가 물질

6

반응물 2

HCID 61436Stannous chloride dihydrateHCID 684666532-Methyl-3-[2-(4-nitro-phenyl)-ethyl]-5,5-diphenyl-3,5-dihydro-imidazol-4-one

생성물 1

HCID 684664113-[2-(4-Amino-phenyl)-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one수율 97.4%

시약·촉매·용매 3

HCID 222Ammonia용매HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A mixture of 2-methyl-3-[2-(4-nitro-phenyl)-ethyl]-5,5-diphenyl-3,5-dihydro-imidazol-4-one (205 mg, 0.5 mmol) and SnCl2.2H2O (591 mg, 2.6 mmol) in 10 mL ethanol is heated to 50° C. for 5 hours. The reaction mixture is cooled to room temperature, diluted with water and aqueous ammonia is added to reach pH 8-9. The mixture is filtered, the filtrate evaporated and the residue purified by flash chromatography. ISCO Companion CombiFlash, 12 g silica gel, methylene chloride/ethanol to yield 3-[2-(4-amino-phenyl)-ethyl]-2-methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one (180 mg, 85%). LC/MS at 254 nm; [M+H] 370; Rt 2.424 min.

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. additionis added
  3. filtrationThe mixture is filtered
  4. customthe filtrate evaporated
  5. customthe residue purified by flash chromatography

출처 및 근거

ORD 기록
ord-9d83dfe6cfc74659985b6b1d82a5ff24
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786155B2

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