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

HRID 247745

반응식

HRID 247745 반응식
[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]

참가 물질

6

반응물 3

HCID 7242O-ToluidineHCID 10340Sodium CarbonateHCID 62493Pivaloyl chloride2회

생성물 1

HCID 27340052,2,2'-Trimethylpropionanilide수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-ba61df26d5534c84b2422beb39b70187
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709093

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