Water → N-(2,4-Dichloropyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamide

HRID 81381Notes

Reaction equation

HRID 81381 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(=O)([O-])O.[Na+].O.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21]>C(OCC)(=O)C>[Cl:8][C:5]1[N:4]=[C:3]([Cl:9])[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[C:24]([CH3:28])[C:25]([O:26][CH3:27])=[C:17]([CH3:16])[CH:18]=2)=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2577975-Amino-2,4-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 214353833,5-Dimethyl-4-methoxybenzoyl chloride

Product 1

HCID 86675952N-(2,4-Dichloropyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamideYield 118.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.2 g of 5-amino-2,4-dichloro-pyrimidine in 50 ml of ethyl acetate was added to a mixture of 25 ml of a saturated aqueous sodium hydrogencarbonate solution and 25 ml of water. A solution of 4.9 g of 3,5-dimethyl-4-methoxy-benzoyl chloride was added at room temperature over a period of 15 min. The mixture was mixed intensively for 4 h. Then the layers were separated and the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration, the solvent was removed in vacuo to give 7.54 g of raw product. The raw product was triturated with 25 ml of isopropanol. After filtration and washing with 10 ml of isopropanol 2.74 g of the title compound was obtained as a white solid.

Workup

  1. additionThe mixture was mixed intensively for 4 h
  2. customThen the layers were separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialAfter drying over sodium sulfate and filtration
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4832a96646f849b39657adba19b1ae56
Source dataset
uspto-grants-2014_09
Patent number
US08846692B2

Reaction notes

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