Potassium Carbonate → 2-(8-Bromooctyl)-4,5-diphenyltriazole

HRID 1376378

反応式

HRID 1376378 の反応式
[C:1]1([C:7]2[N:8]=[N:9][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:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:9]1[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:10]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 783101,8-DibromooctaneHCID 178420171HCID 178420171、化合物

生成物 1

HCID 229163312-(8-Bromooctyl)-4,5-diphenyltriazole収率 54.3%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

A mixture of 4,5-diphenyltriazole (11 g), 1,8-dibromooctane (67.6 g), and potassium carbonate (10.31 g) in dry butanone (300 ml ) was heated at reflux temperature for 24 hours. The mixture was filtered and the solvent evaporated to give an oily residue. Distillation to remove 1,8-dibromooctane and column chromatography on silica gel eluted with a hexane:ethyl acetate gradient gave 2-(8-bromooctyl)-4,5-diphenyl-triazole (11.13 g, 54%) as an oil. NMR d (CDCl3) 1.2-1.5 (8H, m, 4×CH2), 1.84 (2H, m, CH2), 2.05 (2H, m, CH2), 3.37 (2H, t, Br-CH2), 4.47 (2H, t, N-CH2), 7.3- 7.6 (10H, m, 2×Ph) ppm

後処理

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hours
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated
  5. customto give an oily residue
  6. distillationDistillation
  7. customto remove 1,8-dibromooctane and column chromatography on silica gel
  8. washeluted with a hexane

出典と根拠

ORDレコード
ord-2f43627d002d44e28d7c8767ab798787
出典データセット
uspto-grants-1997_09
特許番号
US05663053

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