Triethylamine → Methyl 2-(4-Chlorobenzoylamino)-3,4,5-trimethoxybenzoate

HRID 1166145Notes

Reaction equation

HRID 1166145 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[C:19]([O:26][CH3:27])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[C:19]([O:26][CH3:27])=[CH:18][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 78735Methyl 3,4,5-trimethoxyanthranilate

Product 1

HCID 15406018Methyl 2-(4-Chlorobenzoylamino)-3,4,5-trimethoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 20.3 g of 4-chlorobenzoyl chloride in 60 ml of THF was added dropwise to the solution of 25.3 g of methyl 2-amino-3,4,5-trimethoxybenzoate and 16 ml of triethylamine in 100 ml of THF. The mixture was refluxed for 1 hour (h), cooled in an ice bath and filtered. After concentration, a colorless residue remained. Yield: 34.1 g. Melting point (m.p.): 116° C.

Workup

  1. temperatureThe mixture was refluxed for 1 hour (h)
  2. temperaturecooled in an ice bath
  3. filtrationfiltered
  4. concentrationAfter concentration
  5. custom116° C.

Sources & evidence

ORD record
ord-ccaf1e90c0594ea9894e2dd553034cc7
Source dataset
uspto-grants-2003_09
Patent number
US06613772B1

Reaction notes

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