4-Isopropylbenzyl chloride → 2-[(4-Isopropylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 2053583ノート

反応式

HRID 2053583 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.[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][Cl:27])=[CH:24][CH:23]=1)([CH3:21])[CH3:20]>CCO>[ClH:27].[CH:19]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][S:18][C:9]2[NH:8][C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=2)=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

参加物

4

反応物 2

HCID 749164-Isopropylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

生成物 1

HCID 685707482-[(4-Isopropylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride収率 74.9%

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 4-isopropylbenzyl chloride (264 mg, 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 249 mg of the product 239. 1H NMR (DMSO-d6) δ 11.24 (s, 2H), 7.52 (d, 2H), 7.32 (d, 2H), 7.20-6.90 (m, 6H), 6.90-6.70 (m, 4H), 5.77 (s, 2H), 4.78 (s, 2H), 3.02-3.85 (m, 1H), 1.22 (d, 6H); MS: m/z 387 (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-d3977183eb964dc28870ffeadf4c039c
出典データセット
uspto-grants-2008_02
特許番号
US07326792B2

反応ノート

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