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Phosgene → HCID 72636696, 화합물

HRID 1367703
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HRID 1367703 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH:29]([CH3:31])[CH3:30])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:39](Cl)([Cl:41])=[O:40]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:39]([Cl:41])=[O:40])[C:10]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH:29]([CH3:31])[CH3:30])=[N:9]2)=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 52886301H-Imidazole, 4,5-bis(4-chlorophenyl)-4,5-dihydro-2-[4-methoxy-2-(1-methylethoxy)phenyl]-, (4R,5S)-rel-

생성물 1

HCID 72636696HCID 72636696, 화합물수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of cis-4,5-bis-(4-chloro-phenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole (5 g, 10.98 mmol, example 2) in methylene chloride (50 mL) cooled to 0° C. were added triethylamine (3 mL, 21.96 mL) and phosgene (8.7 mL, 16.47 mmol, ˜20% solution in toluene), respectively. The reaction mixture was stirred at 0° C. for 30 min then the excess reagents and solvent were removed under reduced pressure. The residue was taken in methylene chloride (˜100 mL) and the solution was filtered through a plug of silica gel (˜50 g). The silica gel was washed with 20% ethyl acetate in hexanes. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel, eluting with 5%, 10%, 20% ethyl acetate in hexanes) to give rac-4,5-bis-(4-chloro-phenyl)-2-(2-isopropoxy-4-methoxy-phenyl)-4,5-dihydro-imidazole-1-carbonyl chloride as white solids (4.31 g, 76%).

후처리

  1. customthe excess reagents and solvent were removed under reduced pressure
  2. filtrationthe solution was filtered through a plug of silica gel (˜50 g)
  3. washThe silica gel was washed with 20% ethyl acetate in hexanes
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel, eluting with 5%, 10%, 20% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-c81bd684aa1c4a4db9e5b317fd235a60
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07893278B2

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