Phosgene → HCID 20538679, compound

HRID 1065794Notes

Reaction equation

HRID 1065794 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].C(N(CC)CC)C.[C:19](Cl)([Cl:21])=[O:20]>O1CCCC1>[C:1]([C:5]1[CH:9]=[C:8]([S:10][CH3:11])[N:7]([C:19]([Cl:21])=[O:20])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 178503166HCID 178503166, compound

Product 1

HCID 20538679HCID 20538679, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-t-butyl-5-(methylthio)pyrazole (10 g), and triethylamine (6.0 g) were added dropwise at -20° to a stirred solution of phosgene (7.5 ml) in tetrahydrofuran (75 ml). The solution was allowed to come to room temperature, and was then stirred for 2 hours. Excess phosgene was removed by drawing dry air through the mixture for 1/2 hour. The reaction mixture was filtered, and evaporated to give a yellow oil which quickly crystallised. Recrystallisation from petrol gave 3-tert-butyl-1-chlorocarbonyl-5-(methylthio)pyrazole, 5.0 g (64% yield), melting point 64°-6°.

Workup

  1. customto come to room temperature
  2. customExcess phosgene was removed
  3. customby drawing dry air through the mixture for 1/2 hour
  4. filtrationThe reaction mixture was filtered
  5. customevaporated
  6. customto give a yellow oil which
  7. customquickly crystallised
  8. customRecrystallisation from petrol

Sources & evidence

ORD record
ord-9c75365073ec4321a012c0573e84552a
Source dataset
uspto-grants-1982_05
Patent number
US04331678

Reaction notes

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