Potassium Carbonate → HCID 25217362, compound

HRID 1642752Notes

Reaction equation

HRID 1642752 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(O)(O)(=O)=O.[CH3:33][O:34][C:35](=[NH:37])[NH2:36].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[NH2:37][C:35]([O:34][CH3:33])=[N:36][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:24]([F:26])([F:27])[F:25])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 866114794-(5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl)-2-methylbenzoyl chloride

Product 1

HCID 25217362HCID 25217362, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.00 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl-chloride synthesized in Process 4 of Synthetic Example 1 in 20 mL of acetonitrile, 0.85 g of O-methylisourea sulfate and 1.26 g of potassium carbonate were added and the resultant mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction, the insoluble substance was filtered off and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 0.40 g of the objective substance as a yellow resin-state substance.

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe insoluble substance was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography
  5. washeluting with ethyl acetate-hexane (1:1)
  6. customto obtain 0.40 g of the objective substance as a yellow resin-state substance

Sources & evidence

ORD record
ord-1a9dcc286a904470aa2555f0e7c4554c
Source dataset
uspto-grants-2012_02
Patent number
US08119671B2

Reaction notes

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