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

HRID 1027712Notes

Reaction equation

HRID 1027712 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 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.2 g of 5-amino-2,4-dichloropyrimidine in 50 ml ethyl acetate were added to a mixture of 25 ml of saturated aqueous sodium bicarbonate solution and 25 ml of water. At room temperature, a solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added over a period of 15 min. The mixture was stirred intensively for 4 h. The layers were then separated, after which the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration, the solvent was removed under reduced pressure, giving 7.54 g of crude product. The crude product was triturated with 25 ml of isopropanol. Filtration and washing with 10 ml of isopropanol gave 2.74 g of the title compound in the form of a white solid.

Workup

  1. customThe layers were then separated
  2. extractionafter which the aqueous layer was extracted twice with ethyl acetate
  3. dry with materialAfter drying over sodium sulfate and filtration
  4. customthe solvent was removed under reduced pressure
  5. customgiving 7.54 g of crude product
  6. customThe crude product was triturated with 25 ml of isopropanol
  7. filtrationFiltration
  8. washwashing with 10 ml of isopropanol

Sources & evidence

ORD record
ord-dc6020ee77a54ed0866f1ee00978042f
Source dataset
uspto-grants-2014_05
Patent number
US08735402B2

Reaction notes

Loading…