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

HRID 264706Notes

Reaction equation

HRID 264706 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fdce7d4e72c04bffb1204638a1122797
Source dataset
uspto-grants-1997_07
Patent number
US05646144

Reaction notes

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