Hydrochloric Acid → HCID 18674196, compound

HRID 1635933Notes

Reaction equation

HRID 1635933 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14](=O)[CH2:15][CH3:16])[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:33]2)=CC=1.C1(C)C=CC=CC=1.Cl>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[C:10]([NH:13][C:14](=[S:33])[CH2:15][CH3:16])[C:9]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 87949Lawesson's reagentHCID 15513083HCID 15513083, compound

Product 1

HCID 18674196HCID 18674196, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

175 mg of 5-(4-fluorophenyl)-3-propionylamino-4-(4-pyridyl)pyrazole and 450 mg of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide were added to 30 ml of toluene, followed by heating under reflux for 2 hours. After the reaction mixture was cooled, 10% hydrochloric acid and ethyl acetate were added thereto. The aqueous layer was separated, neutralized with a saturation solution of sodium hydrogen carbonate, and extracted with chloroform-methanol (5:1). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (using chloroform-methanol (10:1) as the developing solvent). Thus, 113 mg (61% yield) of the title compound was obtained as pale-yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter the reaction mixture was cooled
  4. customThe aqueous layer was separated
  5. extractionextracted with chloroform-methanol (5:1)
  6. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel thin-layer chromatography (

Sources & evidence

ORD record
ord-23f57658ec904d07bbf7fcdd34f549c4
Source dataset
uspto-grants-2003_01
Patent number
US06511997B1

Reaction notes

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