Ethyl chloroformate → 3-Chloro-5-[[(ethoxycarbonyl)amino]sulfonyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1789575Notes

Reaction equation

HRID 1789575 reaction equation
[Cl:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([S:12]([NH2:15])(=[O:14])=[O:13])[N:4]([CH3:16])[N:3]=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:21]([O:20][C:18]([NH:15][S:12]([C:5]1[N:4]([CH3:16])[N:3]=[C:2]([Cl:1])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:14])=[O:13])=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 13687032Ethyl 5-(aminosulfonyl)-3-chloro-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 136870373-Chloro-5-[[(ethoxycarbonyl)amino]sulfonyl]-1-methyl-1H-pyrazole-4-carboxylic acid ethyl esterYield 88.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into 30 ml of dry acetone, there were added 5.35 g of 3-chloro-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide, 2.5 g of ethyl chloroformate and 4.14 g of anhydrous potassium carbonate and the mixture was refluxed for three hours. After cooling, acetone was evaporated and the residue was added into ice-water. After separation of a trace of water insolubles, the filtrate was made acidic with hydrochloric acid. The reaction mixture was extracted with diethyl ether and organic layer was dried and the solvent was evaporated under reduced pressure to give 6.0 g of N-(ethoxycarbonyl)-3-chloro-4-ethoxycarbonyl-1-methylpyrazole-5-sulfonamide. m.p.: 82°-85° C.

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. temperatureAfter cooling
  3. customacetone was evaporated
  4. additionthe residue was added into ice-water
  5. customAfter separation of a trace of water insolubles
  6. extractionThe reaction mixture was extracted with diethyl ether and organic layer
  7. customwas dried
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4bea319f54e043c18ca1eacb7f516b8c
Source dataset
uspto-grants-1987_08
Patent number
US04689417

Reaction notes

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