Sodium Hydroxide → N-{5-(4-Chlorophenyl)pent-1-en-4-yl}-N-ethoxymethyl-3,5-dimethylbenzamide

HRID 264706

반응식

HRID 264706 반응식
[CH2:1]([O:3][CH2:4]Cl)[CH3:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:9][CH:8]=1.[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:18]([CH2:4][O:3][CH2:1][CH3:2])[C:19](=[O:28])[C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=2)[CH2:15][CH:16]=[CH2:17])=[CH:9][CH:8]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 18523Chloromethyl ethyl etherHCID 19035936N-{5-(4-chlorophenyl)pent-1-en-4-yl}-3.5-dimethylbenzamide

생성물 1

HCID 19035912N-{5-(4-Chlorophenyl)pent-1-en-4-yl}-N-ethoxymethyl-3,5-dimethylbenzamide

시약·촉매·용매 2

HCID 159952Benzyltributylammonium chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

2.36 ml (25.2 mmol) of chloromethyl ethyl ether are added in small portions over the course of 2 hours to a vigorously stirred solution of 5.5 g (16.8 mmol) of N-{5-(4-chlorophenyl)pent-1-en-4-yl}-3.5-dimethylbenzamide and 100 mg of benzyltributylammonium chloride in 15 ml of 50% strength aqueous sodium hydroxide solution and 15 ml of dichloromethane at 0°-5°. The organic phase is taken up in dichloromethane and water, the organic phase is separated off, dried over sodium sulfate and evaporated to dryness under reduced pressure. The oily residue is purified by chromatography on silica gel with ethyl acetate/hexane (1:4) as mobile phase; TLC (ethyl acetate/hexane; 1:3):Rf =0.50; 1H-NMR (300 MHz, CDCl3):mixture of rotamers, δ=7.31-7.18 (m, 4 H), 7.04-6.85 (m, 2.6 H), 6.42 (hr. s, 0.4 H), 5.92-5.60 (m, 1 H), 5.20-5.02 (m, 2 H), 4.54-4.24 (m, 2 H), 3.96-3.67 (m, 1 H), 3.25-2.40 (m, 6 H), 2.28 (s, ca 5 H), 2.24 (s, ca 1 H), 1.34-1.21(m, ca 0.5 H), 1.08 (t, J=7, ca 2.5 H).

후처리

  1. customwater, the organic phase is separated off
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness under reduced pressure
  4. customThe oily residue is purified by chromatography on silica gel with ethyl acetate/hexane (1:4) as mobile phase

출처 및 근거

ORD 기록
ord-fdce7d4e72c04bffb1204638a1122797
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646144

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