Water → HCID 14771500, compound

HRID 1742639Notes

Reaction equation

HRID 1742639 reaction equation
C[N:2]([C:4]([C:26](=O)[CH2:27]C)=[CH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:3].O.[CH3:31][NH:32]N>CO>[CH2:26]([C:4]1[N:2]([CH3:3])[N:32]=[CH:31][C:5]=1[S:6]([C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)(=[O:7])=[O:8])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 54257069HCID 54257069, compound

Product 1

HCID 14771500HCID 14771500, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture composed of 4.3 g (0.01 mole) of 1-(N,N-dimethylamino)-1propionyl 2-(4-tosyloxybenzenesulfonyl)ethene is heated at reflux for 20 hours in 25 ml of methanol and 10 ml of water in the presence of 2.35 g (0.05 mole) of methylhydrazine. The mixture is allowed to cool to room temperature and then cooled in ice for 1 h. It is evaporated to dryness and 4.85 g of residue are thus obtained which are recrystallized from 250 ml of water and decolorized with 0.8 g of active charcoal. The product is filtered off and allowed to crystallize for 2 hours in ice. It is recrystallized again from 50 ml of dichloroethene. In this manner, 1.15 g of 5-ethyl 4-(4-hydroxybenzenesulfonyl)1-methyl pyrazole is obtained which represents a yield of 43.2%. M.p.: 188.5°-190° C.

Workup

  1. temperatureis heated
  2. temperaturecooled in ice for 1 h
  3. customIt is evaporated to dryness and 4.85 g of residue
  4. customare thus obtained which
  5. customare recrystallized from 250 ml of water
  6. filtrationThe product is filtered off
  7. customto crystallize for 2 hours in ice
  8. customIt is recrystallized again from 50 ml of dichloroethene

Sources & evidence

ORD record
ord-af127a76c5334cd29024759f34e9cf46
Source dataset
uspto-grants-1994_08
Patent number
US05340820

Reaction notes

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