Ethyl 5-bromovalerate → 5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid ethyl ester

HRID 1109046ノート

反応式

HRID 1109046 の反応式
[C:1]1([C:7]2[N:8]=[C:9]([SH:18])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][S:18][C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1)[CH3:28]

参加物

5

反応物 3

HCID 84580Ethyl 5-bromovalerateHCID 516892Sodium BicarbonateHCID 178527825HCID 178527825、化合物

生成物 1

HCID 542015795-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid ethyl ester収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Part A. To a solution of 4,5-diphenyl-2-imidazolethiol (25.2 g, 0.1 mol) in N,N-dimethylformamide (250 mL) was added, dropwise, a solution of ethyl 5-bromopentanoate (23.73 mL, 31.35 g, 0.15 mol) in N,N-dimethylformamide (80 mL), and the reaction mixture was stirred at reflux under nitrogen for 18 hours. The reaction mixture was cooled, poured into 5% sodium bicarbonate and ice, and then extracted with ethyl acetate. The combined organic extracts were washed sequentially with 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under vacuum. The residue was chromatographed with 7:3 hexane-ethyl acetate, and the resulting solid was recrystallized from acetonitrile and triturated with hexane to give 5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid ethyl ester (25.95 g, 0.068 mol) as a white solid, mp 87°-89°. 1H NMR (DMSO-d6) δ 7.55-7.15 (m,11H), 4.0(q,2H,J=8 Hz) , 2.9(t,2H,J= 7 Hz) , 2.3(t,2H,J=7 Hz), 1.9-1.6(m,4H), 1.2(t,3H,J=8 Hz).

後処理

  1. temperatureat reflux under nitrogen for 18 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed sequentially with 5% sodium bicarbonate, water, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed with 7:3 hexane-ethyl acetate
  8. customthe resulting solid was recrystallized from acetonitrile
  9. customtriturated with hexane

出典と根拠

ORDレコード
ord-e4b07c28d5184e119fe423db09fdcc6b
出典データセット
uspto-grants-1994_06
特許番号
US05318984

反応ノート

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