Triethylamine → Methyl 4,5-dimethoxy-2-[(3,4,5-trimethoxybenzoyl)amino]benzoate

HRID 1156856Notes

Reaction equation

HRID 1156856 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[C:13](Cl)=[O:14].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH2:37])[C:28](=[CH:33][C:34]=1[O:35][CH3:36])[C:29]([O:31][CH3:32])=[O:30]>C(Cl)(Cl)Cl>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[C:13]([NH:37][C:27]1[C:28](=[CH:33][C:34]([O:35][CH3:36])=[C:25]([O:24][CH3:23])[CH:26]=1)[C:29]([O:31][CH3:32])=[O:30])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 611144Methyl 4,5-dimethoxyanthranilate

Product 1

HCID 1712580Methyl 4,5-dimethoxy-2-[(3,4,5-trimethoxybenzoyl)amino]benzoateYield 79.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In a mixture of 3.2 g of methyl 4,5-dimethoxyanthranilate in 30 ml of chloroform is dissolved 3 ml of triethylamine, and to this solution is added a solution of 3.45 g of 3,4,5-trimethoxybenzoylchloride in chloroform under cooling. The mixture is stirred at room temperature for 4 hours. The reaction mixture is concentrated under a reduced pressure and to the residue is added water. The precipitated crystals are recrystallized from a mixture of dimethylformamide and ethanol to obtain 4.8 g of methyl N-(3,4,5-trimethoxybenzoyl)-4,5-dimethoxyanthranilate as pale yellow prisms.

Workup

  1. temperatureunder cooling
  2. concentrationThe reaction mixture is concentrated under a reduced pressure and to the residue
  3. additionis added water
  4. customThe precipitated crystals are recrystallized from a mixture of dimethylformamide and ethanol

Sources & evidence

ORD record
ord-a15ab01942d546f59deb8100971317b6
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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