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

HRID 511879

反応式

HRID 511879 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-20b46d084097407981a55ad2c4758bf3
出典データセット
uspto-grants-2015_08
特許番号
US09101614B2

関連ノート

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