Acetic Acid → HCID 18549215, compound

HRID 1266201Notes

Reaction equation

HRID 1266201 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][CH2:30][CH2:31][CH3:32])[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][CH2:30][CH2:31][CH3:32])[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 18549227HCID 18549227, compound

Product 1

HCID 18549215HCID 18549215, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sulfuryl chloride (0.011 ml) was added to acetic acid (1.3 ml) solution of 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-butyl-6-trifluoromethyl-4(3H)-pyrimidinone (60 mg, 0.13 mmol) which had been synthesized in accordance with the method of Example 24, followed by stirring at room temperature for 1 hour. After completion of the reaction, ether (20 ml) was saturated sodium bicarbonate aqueous solution (20 ml) were added to the reaction solution to separate the organic layer, and the resulting aqueous layer was extracted with ether (10 ml×2). The thus obtained ether layers were combined, washed with sodium bicarbonate aqueous solution (20 ml) and saturated brine (20 ml), dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By purifying the thus obtained crude product by a silica gel column chromatography (dichloromethane:hexane=10:3), white solid of 2-{2,5-bis(trifluoromethyl)phenyl}amino-3-butyl-5-chloro-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 55] was obtained.

Workup

  1. customhad been synthesized in accordance with the method of Example 24
  2. additionwere added to the reaction solution
  3. customto separate the organic layer
  4. extractionthe resulting aqueous layer was extracted with ether (10 ml×2)
  5. washwashed with sodium bicarbonate aqueous solution (20 ml) and saturated brine (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under a reduced pressure
  8. customBy purifying the

Sources & evidence

ORD record
ord-47f105c80e834456b1412ad45879caac
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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