1-Bromohexane → N-(4-Aminophenyl)-N-hexylacetamide

HRID 1983567

反応式

HRID 1983567 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:6]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:7](=[O:9])[CH3:8])=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 312304-Aminoacetanilide

生成物 1

HCID 57713043N-(4-Aminophenyl)-N-hexylacetamide収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4′-aminoacetanilide (1.00 g, 6.66 mmol) in N,N-dimethylformamide (10 mL) was added sodium hydride (60% dispersion in mineral oil; 0.28 g, 7.0 mmol). After 5-10 minutes, 1-bromohexane was added dropwise to the mixture. The reaction was stirred for one hour and then partitioned between ethyl acetate and water. The organic layer was washed with additional water, dried (sodium sulfate) and concentrated. The resulting brown oil was purified by flash chromatography over silica (methylene chloride/methanol) to afford 1.32 g (84%) of product as a viscous amber oil: 1H NMR (CDCl3) δ 6.91 (d, J=8.7 Hz, 1H), 6.68 (d, J=8.7Hz, 1H), 3.78 (br s, 2H), 3.61 (t, J=7.9Hz, 2H), 1.81 (s, 3H), 1.33-1.18 (m, 2H), 1.17-1.08 (m, 6H), 0.85 (t, J=6.9 Hz, 3H) ppm.

後処理

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with additional water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe resulting brown oil was purified by flash chromatography over silica (methylene chloride/methanol)

出典と根拠

ORDレコード
ord-35b4111d6cad4ddbabfc43a67b491af2
出典データセット
uspto-grants-2009_06
特許番号
US07541466B2

関連ノート

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