Acetyl chloride → HCID 20080361, compound

HRID 1653654Notes

Reaction equation

HRID 1653654 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])N=2)=[CH:4][CH:3]=1.[C:23](=O)([O-])[O-].[K+].[K+].[C:29](Cl)(=[O:31])[CH3:30]>CCC(C)=O>[C:29]([NH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[CH:23]=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([O:19][CH3:20])[N:18]=2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 15239974Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinate

Product 1

HCID 20080361HCID 20080361, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
75 °C

Procedure

318.9 g (1.04 mol) of methyl 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate and 157.6 g (1.14 mol) of potassium carbonate were dissolved in MEK, and 89.8 g (1.14 mol) of acetyl chloride was added thereto at room temperature. The mixture was refluxed under heating (75° C.) for two hours. MEK was concentrated to a half amount and then cooled. The reaction solution was poured into ice water and crystallized. Crystals thereby obtained was collected by filtration and washed with water. The crystals were dissolved in dichloromethane and subjected to liquid separation. The dichloromethane layer was dried over anhydrous magnesium sulfate and then concentrated. A small amount of diisopropyl ether were added thereto, and the mixture was cooled for crystallization. The crystals thereby obtained were recrystallized from 100 ml of ethanol. The crystals thereby obtained were washed with diisopropyl ether and then dried at 50° C. for 24 hours to obtain the desired product as a white powder.

Workup

  1. customat room temperature
  2. temperatureThe mixture was refluxed
  3. concentrationMEK was concentrated to a half amount
  4. temperaturecooled
  5. additionThe reaction solution was poured into ice water
  6. customcrystallized
  7. customCrystals thereby obtained
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. dissolutionThe crystals were dissolved in dichloromethane
  11. customsubjected to liquid separation
  12. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated
  14. additionA small amount of diisopropyl ether were added
  15. temperaturethe mixture was cooled for crystallization
  16. customThe crystals thereby obtained
  17. customwere recrystallized from 100 ml of ethanol
  18. customThe crystals thereby obtained
  19. washwere washed with diisopropyl ether
  20. customdried at 50° C. for 24 hours

Sources & evidence

ORD record
ord-b066d9a8d30740c5bcde7d82d37021c1
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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