Ammonia → Ethyl 1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylate

HRID 1031335Notes

Reaction equation

HRID 1031335 reaction equation
[NH3:1].[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([CH2:13]C)[C:11]=1[SH:12])=[O:6])[CH3:3].[OH-:15].[Na+].[O-:17]Cl.[Na+]>>[CH2:2]([O:4][C:5]([C:7]1[CH:8]=[N:9][N:10]([CH3:13])[C:11]=1[S:12]([NH2:1])(=[O:17])=[O:15])=[O:6])[CH3:3]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 23665760Sodium HypochloriteHCID 178469998HCID 178469998, compound

Product 1

HCID 13364389Ethyl 1-methyl-5-sulfamoyl-1H-pyrazole-4-carboxylate

Procedure

To 100 ml of a 28 % aqueous ammonia, there was added 20 ml of aqueous solution containing 7.1 g of ethyl-5-mercapto-1-ethyl-4-pyrazole carboxylate and 1.6 g of sodium hydroxide. To this reaction mixture was added 61 g of 6 % aqueous NaOCl solution at 5°-10° C. The precipitated crystals were filtered and washed with water. The resultant moist sulfenamide (5.6g) was suspended in water and an aqueous saturated solution of 5.5 g of potassium permanganate was added to the suspension at room temperature. After stirring vigorously at room temperature, the mixture was filtered. The filtrate was made acidic and extracted with ethyl acetate. After drying, the solvent was evaporated to obtain 1.8 g of the title compound. m.p. 102°-104° C.

Workup

  1. filtrationThe precipitated crystals were filtered
  2. washwashed with water
  3. additionan aqueous saturated solution of 5.5 g of potassium permanganate was added to the suspension at room temperature
  4. filtrationthe mixture was filtered
  5. extractionextracted with ethyl acetate
  6. customAfter drying
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-408ad341a8164941af5ab13af6553925
Source dataset
uspto-grants-1990_09
Patent number
US04954164

Reaction notes

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