3,4-Difluorobenzyl Chloride → 2-[(3,4-Difluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18766

반응식

HRID 18766 반응식
[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]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][Cl:24]>CCO>[ClH:24].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[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

참가 물질

4

반응물 2

HCID 27369543,4-Difluorobenzyl ChlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

생성물 1

HCID 685696432-[(3,4-Difluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride수율 63.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3,4-difluorobenzyl chloride (0.255 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 207 mg of the product 214. 1H NMR (DMSO-d6) δ 11.38 (s, 2 H), 7.90-7.65 (m, 1 H), 7.65-7.40 (m, 2 H), 7.20-6.90 (m, 6 H), 6.90-6.65 (m, 4 H), 5.79 (s, 2 H), 4.85 (s, 2 H); MS: m/z 381 (M++1).

후처리

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

출처 및 근거

ORD 기록
ord-8bd6e468d93f4c1da0b2c6c4a3d0a0df
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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