Triethylamine → N-cyclopropyl-4-methyl-3-nitrobenzamide

HRID 403027

反応式

HRID 403027 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH:14]1([NH2:17])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[CH:14]1([NH:17][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 69828Cyclopropylamine

生成物 1

HCID 2162665N-cyclopropyl-4-methyl-3-nitrobenzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4-methyl-3 nitrobenzoyl chloride (20 g) in methylene chloride (200 mL) at 0° C. was added a mixture of cyclopropylamine (7.62 mL) and triethylamine (28 mL). The mixture was allowed to warm to room temperature and stirred for a further 16 hours. The reaction mixture was evaporated in vacuo and a saturated aqueous solution of sodium bicarbonate was added. The precipitated solid was filtered off and washed with isohexane and dried (magnesium sulphate) to give N-cyclopropyl-4-methyl-3-nitrobenzamide as a colourless solid (22.9 g); NMR Spectrum: (DMSOd6) 0.60 (m, 2H), 0.72 (m, 2H), 2.56 (s, 3H), 2.87 (m, 1H), 7.60 (d, 1H), 8.06 (m, 1H), 8.41 (d, 1H), 8.67 (d, 1H); Mass Spectrum: M+H+ 221. B) A suspension of N-cyclopropyl-4-methyl-3-nitrobenzamide (22.92 g) and 10% palladium on carbon (2 g) in absolute alcohol (500 mL) was agitated under a hydrogen atmosphere for 16 hours. The reaction mixture was filtered through diatomaceous earth (Celite®) and the filtrate evaporated to dryness to give the title compound as a colourless solid (17.1 g); NMR Spectrum: (DMSOd6) 0.53 (m, 2H), 0.65 (m, 2H), 2.07 (s, 3H), 2.80 (m, 1H), 6.92 (m, 2H), 7.06 (d, 1H), 8.09 (d, 1H); Mass Spectrum: M+H+ 191.

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. additiona saturated aqueous solution of sodium bicarbonate was added
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with isohexane
  5. dry with materialdried (magnesium sulphate)

出典と根拠

ORDレコード
ord-5f1ad78a699c4efa86e6b8cf0d7e3724
出典データセット
uspto-grants-2014_06
特許番号
US08742124B2

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