Thiophosgene → ST50844634

HRID 849041Notes

Reaction equation

HRID 849041 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[N:4][N:5]([CH3:8])[C:6]=1[CH3:7].[C:10](Cl)(Cl)=[S:11]>C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:8][N:5]1[C:6]([CH3:7])=[C:2]([N:1]=[C:10]=[S:11])[C:3]([CH3:9])=[N:4]1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 1616031,3,5-trimethyl-1H-pyrazol-4-amine

Product 1

HCID 3263055ST50844634Yield 101.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-amino-1,3,5-trimethylpyrazole (1.32 g, 10.6 mmol) in 50 mL each of CHCl3 and saturated aqueous NaHCO3 was treated dropwise with thiophosgene (0.812 mL, 10.6 mmol) and stirred vigorously for 20 minutes. The layers were separated and the organic phase was washed with brine. After drying (Na2SO4), the solvent was evaporated in vacuo to provide the title compound (1.8 g, brown oil) suitable for use directly in the next step.

Workup

  1. customThe layers were separated
  2. washthe organic phase was washed with brine
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-774bde4296584d1e9038dff9f6bcffbf
Source dataset
uspto-grants-2000_01
Patent number
US06011053

Reaction notes

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