3-(Trifluoromethyl)benzyl chloride → 2-[(3-Trifluoromethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18754

反応式

HRID 18754 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:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][Cl:25]>CCO>[ClH:25].[F:19][C:20]([F:29])([F:30])[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][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 697163-(Trifluoromethyl)benzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

生成物 1

HCID 685671332-[(3-Trifluoromethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride収率 55.5%

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 3-trifluoromethylbenzyl chloride (0.243 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 196 mg of the product 202. 1H NMR (DMSO-d6) δ 11.32 (s, 2 H), 8.10-7.65 (m, 4 H), 7.15-6.95 (m, 6 H), 6.90-6.60 (m, 4 H), 5.78 (s, 2 H), 4.93 (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-e67f4e8fc0d9441fbf3b9cfecc6b4d92
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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