Acetic Acid → HCID 18549198, compound

HRID 1266203Notes

Reaction equation

HRID 1266203 reaction equation
S(Cl)([Cl:4])(=O)=O.C(O)(=O)C.[F:10][C:11]([F:39])([F:38])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=1[NH:22][C:23]1[N:28]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:27](=[O:33])[CH:26]=[C:25]([C:34]([F:37])([F:36])[F:35])[N:24]=1.C(=O)(O)[O-].[Na+]>CCOCC>[F:39][C:11]([F:38])([F:10])[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:13]=1[NH:22][C:23]1[N:28]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:27](=[O:33])[C:26]([Cl:4])=[C:25]([C:34]([F:35])([F:36])[F:37])[N:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 18549201HCID 18549201, compound

Product 1

HCID 18549198HCID 18549198, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sulfuryl chloride (0.16 ml) was added to acetic acid (14 ml) solution of 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-isobutyl-6-trifluoromethyl-4(3H)-pyrimidinone (630 mg, 1.41 mmol), followed by stirring at room temperature for 3 hours. After completion of the reaction, ether (50 ml) and saturated sodium bicarbonate aqueous solution (50 ml) were added to the reaction solution to separate the organic layer, and the resulting aqueous layer was extracted with ether (30 ml×2). The thus obtained ether layers were combined, washed with sodium bicarbonate aqueous solution (50 ml) and saturated brine (50 ml) and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By purifying the thus obtained crude product by a column chromatography (dichloromethane:hexane=7:3), white solid of 2-{2,5-bis(trifluoromethyl)phenyl}amino-5-chloro-3-isobutyl-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 57] was obtained.

Workup

  1. additionwere added to the reaction solution
  2. customto separate the organic layer
  3. extractionthe resulting aqueous layer was extracted with ether (30 ml×2)
  4. washwashed with sodium bicarbonate aqueous solution (50 ml) and saturated brine (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customBy purifying the

Sources & evidence

ORD record
ord-5a75e97a4c564f57870943dd5b249a08
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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