Sulfur Dioxide → 4-Ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide

HRID 1638901Notes

Reaction equation

HRID 1638901 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].N([O-])=O.[Na+].[NH2:22]C(N)=O.[S:26](=[O:28])=[O:27]>Cl.O.ClCCCl>[CH2:16]([O:15][C:13]([C:3]1[CH:4]=[N:5][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[C:2]=1[S:26]([NH2:22])(=[O:28])=[O:27])=[O:14])[CH3:17]

Participants

8

Reactant 4

HCID 1119Sulfur DioxideHCID 1176UreaHCID 742041ethyl 5-amino-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 140491554-Ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamideYield 442.5%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

14 g of ethyl 5-amino-1-(2-pyridyl)pyrazole-4-carboxylate was dissolved in 50 ml of conc. hydrochloric acid, and the solution obtained was cooled to -5° C., to which 5.5 g of sodium nitrite dissolved in 10 ml of water was added cropwise, and thereafter, stirred for 10 minutes, followed by addition of 0.6 g of urea. The solution thus obtained was added dropwise at 5° C. to a solution obtained by adding 2 g of sulfur dioxide and 0.6 g of cuprous chloride to 50 ml of 1,2-dichloroethane. After stirring at room temperature for 1 hour, 200 ml of ice water was added thereto, followed by extraction with chloroform. Seperation of the layer of chloroform, washing with water, drying and concentration were then carried out to obtain 13.1 g of the title compound. m.p.: 38° to 42° C.

Workup

  1. customthe solution obtained
  2. additionwas added cropwise
  3. customThe solution thus obtained
  4. additionwas added dropwise at 5° C. to a solution
  5. customobtained
  6. stirringAfter stirring at room temperature for 1 hour
  7. extractionfollowed by extraction with chloroform
  8. customSeperation of the layer of chloroform
  9. washwashing with water
  10. customdrying
  11. concentrationconcentration

Sources & evidence

ORD record
ord-773eff48afd642c5b2023ff997938c3a
Source dataset
uspto-grants-1989_11
Patent number
US04881965

Reaction notes

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