Propyl mercaptan → HCID 59516103, compound

HRID 1799405Notes

Reaction equation

HRID 1799405 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].[CH2:31]([SH:34])[CH2:32][CH3:33].C(OCC)(=O)C>C(#N)CCC>[CH3:17][O:16][C:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:2]([S:34][CH2:31][CH2:32][CH3:33])=[C:3]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:4]=[N:5]2)=[CH:8][CH:9]=1)=[O:15]

Participants

6

Reactant 4

HCID 7848Propyl mercaptanHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 59516128HCID 59516128, compound2×

Product 1

HCID 59516103HCID 59516103, compound

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Conditions

Temperature
90 °C

Procedure

tert-butyl 5-chloro-1-[4-(methoxycarbonylmethyl)phenyl]pyrazole-4-carboxylate (Intermediate #37) (767 mg, 2.19 mmol) was dissolved in butyronitrile (10 mL). Potassium carbonate (906 mg, 6.57 mmol) and propanethiol (284 μL, 2.74 mmol) were added and the mixture heated at 90° C. for 18 h. The reaction mixture was cooled to ambient and ethyl acetate (50 mL) was added. The mixture was washed with water (4×25 mL), dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (elution gradient 0-25% EtOAc in isohexane) to afford tert-butyl 1-[4-(methoxycarbonylmethyl)phenyl]-5-propylsulfanyl-pyrazole-4-carboxylate as a yellow oil. (527 mg, 62%).

Workup

  1. additionwas added
  2. washThe mixture was washed with water (4×25 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel (elution gradient 0-25% EtOAc in isohexane)

Sources & evidence

ORD record
ord-536795a54eee4ac49688795e28078999
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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