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

HRID 1062428

反応式

HRID 1062428 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-886d796e2ebf4b25bc60492aad07d703
出典データセット
uspto-grants-2005_11
特許番号
US06960601B2

関連ノート

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