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

HRID 507402

反応式

HRID 507402 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 222Ammonia溶媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d83dfe6cfc74659985b6b1d82a5ff24
出典データセット
uspto-grants-2010_08
特許番号
US07786155B2

関連ノート

読み込み中…