2-Propanethiol → HCID 19005830, compound

HRID 1742805Notes

Reaction equation

HRID 1742805 reaction equation
[Cl:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5](Cl)[N:4]([CH3:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:19]([SH:22])([CH3:21])[CH3:20].C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([S:22][CH:19]([CH3:21])[CH3:20])[N:4]([CH3:12])[N:3]=1

Participants

6

Reactant 4

HCID 63642-PropanethiolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10727095HCID 10727095, compound

Product 1

HCID 19005830HCID 19005830, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

30 g of methyl 3,5-dichloro-1-methylpyrazol-4-ylcarboxylate and 25.5 g of potassium carbonate are suspended in 150 ml of DMSO and to this suspension are slowly added 16.1 ml of isopropylmercaptan at a temperature of 25° to 35° C. After stirring for 3 hours at room temperature, the reaction mixture is poured into 200 ml of ice-water and then 300 ml of ethyl acetate are added. After phase separation, the organic phase is washed with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride, dried over MgSO4 and concentrated to dryness under vacuum. Distillation of the residue (113°-114° C., 2×10-3 bar) gives 31.5 g of 3-chloro-4-(methoxycarbonyl)-1-methyl-5-isopropylthiopyrazole in the form of a pale yellow oil.

Workup

  1. customat a temperature of 25° to 35° C
  2. customAfter phase separation
  3. washthe organic phase is washed with 100 ml of water and 100 ml of a saturated aqueous solution of sodium chloride
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness under vacuum
  6. distillationDistillation of the residue (113°-114° C., 2×10-3 bar)

Sources & evidence

ORD record
ord-0c232e6d4d884126bbbe897514991ea6
Source dataset
uspto-grants-1994_08
Patent number
US05342823

Reaction notes

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