Benzimidazole → 2-benzimidazol-1-yl-N-(4-bromophenyl)-acetamide

HRID 1455616ノート

反応式

HRID 1455616 の反応式
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:4].[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:13]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=2)=[O:4])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

参加物

5

反応物 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 2255262-Bromo-n-(4-bromophenyl)acetamide

生成物 1

HCID 170284752-benzimidazol-1-yl-N-(4-bromophenyl)-acetamide収率 63.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Bromo-N-(4-bromophenyl)-acetamide (3.083 g, 10.522 mmol), prepared according to J. Med. Chem., 1996, 4(2), 197-203, benzimidazole (1.24 g, 10.52 mmol) and K2CO3 were combined and dissolved in DMF (60 mL) under nitrogen. The reaction mixture was stirred at room temperature overnight before filtering and purifing by SCX cartridge. The crude product thus obtained was washed with EtOAc to remove excess benzimidazole, yielding the pure product (2.20 g, 63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.17 (2H, s), 7.19-7.28 (2H, m), 7.51 (2H, d, J=12 Hz), 7.51-7.56 (1H, m), 7.57 (2H, d, J=12 Hz), 7.66 (1H, d, J=8 Hz), 8.22 (1H, s), 10.57 (1H, s). MS (ES) m/z: 332.5 [M+H].

後処理

  1. filtrationbefore filtering
  2. customThe crude product thus obtained
  3. washwas washed with EtOAc
  4. customto remove excess benzimidazole

出典と根拠

ORDレコード
ord-63ee8bd55d7d41fba75081141da18398
出典データセット
uspto-grants-2009_01
特許番号
US07482469B2

反応ノート

読み込み中…