Butyl isocyanate → N-(n-butylcarbamoyl)-4-ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide

HRID 1638908Notes

Reaction equation

HRID 1638908 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:10]=1[S:11]([NH2:14])(=[O:13])=[O:12])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:27]([N:31]=[C:32]=[O:33])[CH2:28][CH2:29][CH3:30]>CC(C)=O>[CH2:27]([NH:31][C:32]([NH:14][S:11]([C:10]1[N:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[N:8]=[CH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])(=[O:13])=[O:12])=[O:33])[CH2:28][CH2:29][CH3:30]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 140491554-Ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide

Product 1

HCID 19839374N-(n-butylcarbamoyl)-4-ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamideYield 95.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 70 ml acetone mixture of 8.5 g of 4-ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide and 6.0 g of anhydrous potassium carbonate, added was 3.3 g of n-butylisocyanate at room temperature, followed by heating under reflux for 3 hours. After the reaction was completed, acetone was evaporated under reduced pressure, and then the residue was emptied into ice water to filter insolbles off, and then the filtrate was precipitated with hydrochloric acid. Crystals precipitated was filtered, washed with water and dried to obtain 10.8 g of N-(n-butylcarbamoyl)-4-ethoxycarbonyl-1-(2-pyridyl)pyrazole-5-sulfonamide. m.p.: 180° to 181° C.

Workup

  1. additionadded
  2. customat room temperature
  3. temperatureby heating
  4. temperatureunder reflux for 3 hours
  5. customacetone was evaporated under reduced pressure
  6. filtrationto filter insolbles off, and then the filtrate
  7. customwas precipitated with hydrochloric acid
  8. customCrystals precipitated
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-f49a1aa730cb47e18a9058c083cdc71e
Source dataset
uspto-grants-1989_11
Patent number
US04881965

Reaction notes

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