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

HRID 1983567

반응식

HRID 1983567 반응식
[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

참가 물질

5

반응물 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 312304-Aminoacetanilide

생성물 1

HCID 57713043N-(4-Aminophenyl)-N-hexylacetamide수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-35b4111d6cad4ddbabfc43a67b491af2
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07541466B2

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