2,6-Dimethylaniline → N-(2,6-Dimethylphenyl)-4-nitrobenzamide

HRID 973709

Reaction equation

HRID 973709 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>O1CCCC1>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 477704N-(2,6-Dimethylphenyl)-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.09 moles of 2,6-dimethyl-aniline in 35 ml of tetrahydrofuran was added to 200 ml of 20% (w/v) aqueous potassium carbonate contained in a one liter flask. A solution of 20 g of p-nitrobenzoyl chloride in 35 ml of tetrahydrofuran was added dropwise. The resulting mixture was refluxed for 12 hours while the pH was maintained at or above pH 8. The solution was cooled to room temperature and extracted three times, each with 100 ml of chloroform. The extracts were combined, dried over magnesium sulfate, and evaporated in vacuo. The resulting residue was crystallized from petroleum ether/benzene affording 15 g of the desired subtitle intermediate, m.p. 192-194.

Workup

  1. customcontained in a one liter flask
  2. temperatureThe resulting mixture was refluxed for 12 hours while the pH
  3. temperaturewas maintained at or above pH 8
  4. extractionextracted three times
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was crystallized from petroleum ether/benzene affording 15 g of the desired subtitle intermediate, m.p. 192-194

Sources & evidence

ORD record
ord-a1d3ec810ca944548d66c9da4648afa1
Source dataset
uspto-grants-1991_11
Patent number
US05064862

Linked notes

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