O-Toluidine → 2,2,2'-Trimethylpropionanilide

HRID 247745

反応式

HRID 247745 の反応式
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)Cl.O>[CH3:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15]

参加物

6

反応物 3

HCID 7242O-ToluidineHCID 10340Sodium CarbonateHCID 62493Pivaloyl chloride2 回

生成物 1

HCID 27340052,2,2'-Trimethylpropionanilide収率 93%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A biphasic solution of o-toluidine (107.2 g, 1.0 mol) in methylene chloride (500 ml) and water (150 ml) containing sodium carbonate (69 g, 0.65 mol) was treated with trimethylacetyl chloride (120.6 g, 1.0 mol). The rate of addition of trimethylacetyl chloride was adjusted so as to maintain the reaction at gentle reflux. After 45 minutes the addition was complete. The organic layer was separated, washed with water, and concentrated in vacuo. The crude N-[(2-methyl)phenyl]-2,2-dimethylpropanamide was slurried in 2% aqueous HCl, filtered and washed with H2O until the filtrate was neutral. After drying in vacuo (50° C., 20 mm), N-[(2-methyl)phenyl]-2,2-dimethylpropanamide (178 g, 0.93 mol) was obtained in 93% yield. (mp 109°-110° C.).

後処理

  1. temperatureto maintain
  2. customthe reaction at gentle reflux
  3. additionAfter 45 minutes the addition
  4. customThe organic layer was separated
  5. washwashed with water
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. washwashed with H2O until the filtrate
  9. customAfter drying in vacuo (50° C., 20 mm)

出典と根拠

ORDレコード
ord-ba61df26d5534c84b2422beb39b70187
出典データセット
uspto-grants-1987_11
特許番号
US04709093

関連ノート

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