Triethylamine → Pentafluorophenyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1h-imidazole-4-carboxylate

HRID 1062428

반응식

HRID 1062428 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N:12]=1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[F:42][C:43]1[C:48](O)=[C:47]([F:50])[C:46]([F:51])=[C:45]([F:52])[C:44]=1[F:53]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)[CH:10]=[C:11]([C:13]([O:15][C:48]2[C:47]([F:50])=[C:46]([F:51])[C:45]([F:52])=[C:44]([F:53])[C:43]=2[F:42])=[O:14])[N:12]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 218688042-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid

생성물 1

HCID 22285599Pentafluorophenyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1h-imidazole-4-carboxylate수율 33.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step 1, 2-(2-Chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylic acid (1.5 g, 4.5 mmol) was dissolved in dichloromethane (40 mL). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 946 mg, 4.95 mmol) and triethylamine (500 mg, 4.95 mmol) were added followed by pentafluorophenol (815 mg, 4.37 mmol). The mixture was stirred at rt under argon for one hour before it was washed with 5% HCl, sodium bicarbonate solution, and then brine. The organic layer was dried (MgSO4), filtered, and concentrated to give the crude product (1.26 g) which was chromatographed over silica gel (20% EtOAc in hexanes) to afford pentafluorophenyl 2-(2-chlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (0.73 g, 32% yield): LC-MS m/z 499.0 (MH+), retention time 3.93 min (method 1).

후처리

  1. washwas washed with 5% HCl, sodium bicarbonate solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product (1.26 g) which
  6. customwas chromatographed over silica gel (20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-886d796e2ebf4b25bc60492aad07d703
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960601B2

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