Hexane → HCID 18549200, compound

HRID 1266208Notes

Reaction equation

HRID 1266208 reaction equation
CCCCCC.S(Cl)([Cl:10])(=O)=O.[CH2:12]([N:15]1[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=[C:16]1[NH:26][C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:28]=1[C:37]([F:40])([F:39])[F:38])[CH:13]=[CH2:14].C(=O)(O)[O-].[Na+]>CCOCC.C(O)(=O)C>[CH2:12]([N:15]1[C:20](=[O:21])[C:19]([Cl:10])=[C:18]([C:22]([F:25])([F:23])[F:24])[N:17]=[C:16]1[NH:26][C:27]1[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=[CH:29][C:28]=1[C:37]([F:40])([F:39])[F:38])[CH:13]=[CH2:14]

Participants

7

Reactant 4

HCID 8058HexaneHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 18549207HCID 18549207, compound

Product 1

HCID 18549200HCID 18549200, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

At room temperature, hexane solution of sulfuryl chloride (1.2 M, 0.56 ml, 0.67 mmol) was added to a mixture of 3-allyl-2-(2,5-bis(trifluoromethyl)phenyl)amino-6-trifluoromethyl-4-(3H)-pyrimidinone (0.29 g, 0.67 mmol) and acetic acid (6 ml), followed by stirring for 1 hour. After completion of the reaction, ether (30 ml) and saturated sodium bicarbonate aqueous solution (10 ml) were added to the reaction solution to separate the organic layer, and the resulting aqueous layer was extracted with ether (20 ml×2). The organic layers were combined, washed with saturated sodium bicarbonate aqueous solution and saturated brine in that order and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the solvent was evaporated under a reduced pressure from the resulting filtrate. By purifying the thus obtained crude product by a silica gel column chromatography (hexane:ethyl acetate=3:1), 3-allyl-2-{2,5-bis(trifluoromethyl)phenyl}amino-5-chloro-6-trifluoromethyl-4(3H)-pyrimidinone [Compound No. 67] was obtained as a white solid.

Workup

  1. additionwere added to the reaction solution
  2. customto separate the organic layer
  3. extractionthe resulting aqueous layer was extracted with ether (20 ml×2)
  4. washwashed with saturated sodium bicarbonate aqueous solution and saturated brine in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe solvent was evaporated under a reduced pressure from the resulting filtrate
  8. customBy purifying the

Sources & evidence

ORD record
ord-5c9becf8edb94b49ba6c99de8f79391b
Source dataset
uspto-grants-2003_04
Patent number
US06548511B1

Reaction notes

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