Ethanol → HCID 178470496, compound

HRID 1012131Notes

Reaction equation

HRID 1012131 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[C:9]([C:13]([OH:15])=[O:14])=[N:10][NH:11][CH:12]=1)([O-:7])=[O:6].[CH3:16][CH2:17]O>>[CH2:16]([O:14][C:13]([C:9]1[C:8]([N+:5]([O-:7])=[O:6])=[CH:12][NH:11][N:10]=1)=[O:15])[CH3:17]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 178524956HCID 178524956, compound

Product 1

HCID 178470496HCID 178470496, compound

Procedure

Thionyl chloride (3.8 ml, 52.5 mmol) was added cautiously to a stirred, ice-cold mixture of 4-nitropyrazole-3-carboxylic acid (7.5 g, 47.7 mmol) in EtOH (150 ml), the mixture stirred at ambient temperature for 1 hour then heated at reflux for 3 hours. The reaction mixture was cooled, evaporated in vacuo then azeotroped with toluene to give 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester (8.8 g).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. customevaporated in vacuo
  5. customthen azeotroped with toluene

Sources & evidence

ORD record
ord-aceb58d8ddd446158e1bf1b5609acc3e
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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