Acetic Acid → HCID 11150264, compound

HRID 1935976Notes

Reaction equation

HRID 1935976 reaction equation
[Na][CH:2]([C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3]([O:5]C)=O.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.C(O)(=O)C>C1(C)C(C)=CC=CC=1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]([CH2:2][C:3]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[O:5])=[O:16])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7813p-ToluidineHCID 178501491HCID 178501491, compound

Product 1

HCID 11150264HCID 11150264, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

A solution of the methyl 2-sodio-2(4′-methoxybenzoyl) acetate salt prepared in Example 1(44.60 g, 0.194 mol) and 4-toluidine (20.85 g, 0.195 mol) in xylene (300 ml) was stirred and heated over 1 hour. Glacial acetic acid (11.7 g, 0.195 mol) in xylene (100 ml) was added which caused the mixture to become viscous. The mixture was then heated at reflux for 6 hours and allowed to cool to room temperature. Xylene (200 ml) was added to reduce the viscosity of the mixture. This solution was heated at reflux for 4 hours and allowed to cool to room temperature. The solid N-(4′-methoxybenzoylacetyl)-4-methylaniline product obtained was collected by filtration and washed with toluene and heptane. After removal of the residual organic solvent by drying, the solid product was re-suspended with water (250 ml) and stirred. The solid product was collected by filtration and dried (7.13 g, 13%); m.p. 122-126° C. The solvent was removed from the filtrate. The residue crystallized upon standing and was recrystallized in ethanol to give an additional purified solid product (6.83 g, 12 wt. %); m.p. 127-130° C.

Workup

  1. temperatureheated over 1 hour
  2. temperatureThe mixture was then heated
  3. temperatureat reflux for 6 hours
  4. temperatureThis solution was heated
  5. temperatureat reflux for 4 hours
  6. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-6cc01642ada347d886d24f91562bd7ec
Source dataset
uspto-grants-2002_05
Patent number
US06388093B1

Reaction notes

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