Acetic Acid → HCID 18549190, compound

HRID 1266200Notes

Reaction equation

HRID 1266200 reaction equation
CCCCCC.S(Cl)([Cl:10])(=O)=O.C(O)(=O)C.[F:16][C:17]([F:43])([F:42])[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=1[NH:28][C:29]1[N:34]([CH2:35][CH3:36])[C:33](=[O:37])[CH:32]=[C:31]([C:38]([F:41])([F:40])[F:39])[N:30]=1>CCOCC>[F:43][C:17]([F:42])([F:16])[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:20][C:19]=1[NH:28][C:29]1[N:34]([CH2:35][CH3:36])[C:33](=[O:37])[C:32]([Cl:10])=[C:31]([C:38]([F:39])([F:40])[F:41])[N:30]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8058HexaneHCID 24648Sulfuryl chlorideHCID 185492182-{2,5-bis(trifluoromethyl)phenyl}amino-3-ethyl-6-trifluoromethyl-4(3H)-pyrimidinone

Product 1

HCID 18549190HCID 18549190, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

While stirring under ice-cooling, 10% hexane solution of sulfuryl chloride (0.019 ml, 0.24 mmol) was added to acetic acid (3 ml) solution of 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-ethyl-6-trifluoromethyl-4(3H)-pyrimidinone (0.10 g, 0.24 mmol), followed by stirring for 1.5 hours while gradually returning to room temperature. After completion of the reaction, ice-water (10 ml) and ether (10 ml) were added to the reaction solution to separate the organic layer, and the resulting aqueous layer was extracted with ether (10 ml×3). The organic layers were combined, washed with water (20 ml×2) and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the resulting filtrate was concentrated under a reduced pressure. By recrystallizing the thus obtained crude product from chloroform/hexane, 2-{2,5-bis(trifluoromethyl)phenyl}amino-5-chloro-3-ethyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 49] was obtained.

Workup

  1. temperaturecooling
  2. stirringby stirring for 1.5 hours
  3. customwhile gradually returning to room temperature
  4. additionwere added to the reaction solution
  5. customto separate the organic layer
  6. extractionthe resulting aqueous layer was extracted with ether (10 ml×3)
  7. washwashed with water (20 ml×2)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe drying agent was removed by filtration
  10. concentrationthe resulting filtrate was concentrated under a reduced pressure
  11. customBy recrystallizing the
  12. customthus obtained crude product from chloroform/hexane

Sources & evidence

ORD record
ord-8d0a9e0e5fb947d6b6d3a73ec547a54c
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

Loading…