2-Propanethiol → HCID 59739585, compound

HRID 1192971Notes

Reaction equation

HRID 1192971 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH:8]([SH:10])[CH3:9].Cl[C:12]1[N:16]([CH3:17])[N:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=1[CH:22]=[O:23]>CN(C=O)C>[CH:8]([S:10][C:12]1[N:16]([CH3:17])[N:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[C:13]=1[CH:22]=[O:23])([CH3:9])[CH3:7]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 11430Potassium CarbonateHCID 14784595-Chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 59739585HCID 59739585, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Potassium carbonate (1.68 g, 12 mmol) was suspended in DMF (50 ml) and isopropylthiol (1 ml, 11 mmol) added. The suspension was stirred at room temperature for 15 minutes before a solution of 5-chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbaldehyde (2.12 g, 10 mmol) in DMF (5 ml) was added. The reaction was stirred at room temperature for 16 hours. The reaction was partitioned between aqueous ammonium chloride solution and diethyl ether and the two phases were separated. The organic phase was washed with water and brine, dried over sodium sulfate and concentrated to give the product (2.584 g, 100% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3): 1.29 (3H, s, Me), 1.31 (3H, s, Me), 3.52 (1H, heptet, CH), 4.02 (3H, s, Me), 10.03 (1H, s, CH).

Workup

  1. additionwas added
  2. customThe reaction was partitioned between aqueous ammonium chloride solution and diethyl ether
  3. customthe two phases were separated
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e5a51810f8be47bfb99dcd9c5fa7f55f
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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