o-Phenetidine → N-(2-Ethoxyphenyl)-2-methylbenzamide

HRID 1578620

反応式

HRID 1578620 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Br)=[O:5].[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16])[CH3:12].C(=O)(O)[O-].[Na+]>CC(C)=O>[CH2:11]([O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])[CH3:12]

参加物

5

反応物 3

HCID 7203o-PhenetidineHCID 516892Sodium BicarbonateHCID 2753161o-Methylbenzoyl bromide2 回

生成物 1

HCID 576828N-(2-Ethoxyphenyl)-2-methylbenzamide収率 94.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
40 °C

実験手順

A 19.9 g (0.1 mol) portion of o-methylbenzoyl bromide was added dropwise with cooling to a mixture of 13.7 g (0.1 mol) of o-ethoxyaniline and 8.4 g (0.1 mol) of sodium bicarbonate in 200 ml of acetone with stirring. After addition of the o-methylbenzoyl bromide, the reaction mixture was warmed to 40°C and the mixture was refluxed and stirred for another 40 hours. After filtering, the ether was distilled from the reaction mixture and the residual material was re-dissolved in ether and washed with water. The ether layer was dried over anhydrous sodium sulfate, the ether was removed and the product was distilled to obtain 24.1 g (94.5%) of a clear pink liquid having a boiling point of 148°C/0.04 mm Hg and nD20 of 1.5929. IR cm-1 (film) νNH 3295(S), νCO 1655,1615(S).

後処理

  1. temperaturethe mixture was refluxed
  2. stirringstirred for another 40 hours
  3. filtrationAfter filtering
  4. distillationthe ether was distilled from the reaction mixture
  5. dissolutionthe residual material was re-dissolved in ether
  6. washwashed with water
  7. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  8. customthe ether was removed
  9. distillationthe product was distilled

出典と根拠

ORDレコード
ord-068254ea085449c08e495f0b93f9ea15
出典データセット
uspto-grants-1976_02
特許番号
US03937840

関連ノート

読み込み中…