ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Potassium Carbonate → [3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

HRID 1643220
ノート
印刷プレビュー

反応式

HRID 1643220 の反応式
[CH2:1]([N:5]1[C:9]([CH2:10]O)=[C:8]([C:12]2[CH:17]=[CH:16][C:15](OC)=[CH:14][CH:13]=2)[N:7]=[C:6]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH:30]1([CH2:36][NH2:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[C:38](=[O:41])([O-])[O-].[K+].[K+]>ClCCl.C(#N)C.C(OCC)(=O)C>[CH2:1]([N:5]1[C:9]([CH2:10][NH:37][CH2:36][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:41][CH3:38])=[CH:14][CH:13]=2)[N:7]=[C:6]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 76688CyclohexanemethylamineHCID 588180923-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol

生成物 1

HCID 58818024[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

試薬・触媒・溶媒 3

HCID 6342
Acetonitrile
溶媒
HCID 6344Dichloromethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol (6.72 g, 20 mmol) is dissolved in 30 ml dichloromethane and cooled to 0° C., to the solution is added 5 equivalent of thionyl chloride. The resulting solution is stirred at room temperature for 2 h, the solvent and excess of thionyl chloride is evaporated. 20 ml of toluene is added to the residue and evaporated again to remove the remained thionyl chloride. The residual crude product is dissolved in 30 ml of anhydrous acetonitrile and added to an ice-cooled solution of cyclohexanemethyl amine (2.0 eq.) in 20 ml of acetonitrile containing, 2 equivalent of potassium carbonate. The resulting mixture is stirred at room temperature for 4 h, then diluted with 200 ml of ethyl acetate, washed with water and brine, dried and concentrated, the residue is purified through silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1) to give 11.26 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine. 1H NMR (400 MHz, CDCl3) δ 7.64˜7.60 (4H, m), 7.47˜7.40 (3H, m), 6.94 (2H, d, J=8.8 Hz), 4.11 (2H, m), 3.87 (2H, s), 3.84 (3H,s), 2.52 (H, d, J=6.4 Hz), 0.91˜1.77 (15H, m), 0.84 (3H, t, J=7.2 Hz); MS (+VE) m/z 432 (M+1).

後処理

  1. customthe solvent and excess of thionyl chloride is evaporated
  2. addition20 ml of toluene is added to the residue
  3. customevaporated again
  4. customto remove the remained thionyl chloride
  5. dissolutionThe residual crude product is dissolved in 30 ml of anhydrous acetonitrile
  6. additionadded to an ice-
  7. stirringThe resulting mixture is stirred at room temperature for 4 h
  8. washwashed with water and brine
  9. customdried
  10. concentrationconcentrated
  11. customthe residue is purified through silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1)

出典と根拠

ORDレコード
ord-0c2d20128dd24cefb7cf6b011f951719
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08119665B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート