1-(Chloromethyl)-2-(trifluoromethyl)benzene → (4S,5R)-4,5-diphenyl-2-[[2-(trifluoromethyl)phenyl]methylsulfanyl]-4,5-dihydro-1H-imidazole;hydrochloride

HRID 18784

反応式

HRID 18784 の反応式
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][Cl:24]>CCO>[ClH:24].[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][S:18][C:9]1[NH:8][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1

参加物

4

反応物 2

HCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

生成物 1

HCID 68568953(4S,5R)-4,5-diphenyl-2-[[2-(trifluoromethyl)phenyl]methylsulfanyl]-4,5-dihydro-1H-imidazole;hydrochloride収率 63.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-trifluoromethylbenzyl chloride (0.229 mL, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 224 mg of the product 233. 1H NMR (DMSO-d6) δ 11.41 (s, 2 H), 7.95 (d, 1 H), 7.90-7.75 (m, 2 H), 7.65 (t, 1 H), 7.25-6.90 (m, 10 H), 5.85 (s, 2 H), 4.98 (s, 2 H); MS: m/z 413 (M++1).

後処理

  1. customevaporated to dryness
  2. filtrationThe insoluble material is filtered

出典と根拠

ORDレコード
ord-f12847919b034ad8a458811cb4181326
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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