Ethanol → N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide

HRID 511879

반응식

HRID 511879 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15].[CH2:17](O)C>ClCCl.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]([CH3:17])[C:13](=[O:16])[CH2:14][CH3:15]

참가 물질

5

반응물 2

HCID 702EthanolHCID 2176144N-(2-methoxy-5-nitrophenyl)propanamide

생성물 1

HCID 59167877N-(2-Methoxy-5-nitro-phenyl)-N-methyl-propionamide수율 31%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6344Dichloromethane용매

실험 절차

A solution of 340 mg of N1-(2-methaxy-5-nitrophenyl)-N1, N2, N2-trimethylethane-1,2-diamine (2) in 20 mL of ethanol containing 5% w/w of Pd—C (10%) was subjected to hydrogenation (1 atm, balloon) for 1.5 h. The contents of the flask were passed through a short pad of celite and washed with MeOH. The filtrate was evaporated under reduced pressure and crude amine obtained was carried over to the next reaction without further purification. Thiocarbodiimidazole (260 mg, 1.46 mmol) was added to the crude amine in dichloromethane (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h, and concentrated. The crude product was then purified by flash chromatography on silica gel to give N1-(5-isothiocyanato-2-methoxyphenyl)-)-N1, N2, N2-trimethylethane-1,2-diamine (3) (110 mg, 0.42 mmol, 31%).

후처리

  1. washwashed with MeOH
  2. customThe filtrate was evaporated under reduced pressure and crude amine
  3. customobtained
  4. customwas carried over to the next reaction without further purification
  5. concentrationconcentrated
  6. customThe crude product was then purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-20b46d084097407981a55ad2c4758bf3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09101614B2

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