Dimethylcarbamoyl Chloride → HCID 20538681, compound

HRID 1065791Notes

Reaction equation

HRID 1065791 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([S:10][CH3:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[O:15]>N1C=CC=CC=1>[C:1]([C:5]1[CH:9]=[C:8]([S:10][CH3:11])[N:7]([C:14](=[O:15])[N:13]([CH3:17])[CH3:12])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 178503166HCID 178503166, compound

Product 1

HCID 20538681HCID 20538681, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-t-butyl-5-methylthiopyrazole (6.0 g) and dimethylcarbamoyl chloride (4.3 g) in pyridine (40 ml) were refluxed (at 115° C.) for 16 hours. The pyridine was evaporated, and the residue poured into water and extracted with chloroform. The chloroform layer was washed with 2 N HCl (2×50 ml), then water (50 ml), dried and evaporated to give an oil which soon crystallised. Recrystallisation from 60°-80° petrol at 0° C. gave 5.0 g of 3-t-butyl-1-(dimethylcarbamoyl)-5-(methylthio)pyrazole (59% yield), melting point 56°-8°. Only a single isomer was shown to be present by nuclear magnetic resonance spectroscopy (NMR) and thin layer chromatography.

Workup

  1. customThe pyridine was evaporated
  2. additionthe residue poured into water
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with 2 N HCl (2×50 ml)
  5. dry with materialwater (50 ml), dried
  6. customevaporated
  7. customto give an oil which
  8. customsoon crystallised
  9. customRecrystallisation from 60°-80° petrol at 0° C.

Sources & evidence

ORD record
ord-e032b136970f4c93bd010599a6690003
Source dataset
uspto-grants-1982_05
Patent number
US04331678

Reaction notes

Loading…