Ethanol → HCID 178470496, compound

HRID 659790Notes

Reaction equation

HRID 659790 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, compoundYield 96%

Procedure

Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96%). (1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, 1H), 9.0 (s, 1H), 4.4 (q, 2H), 1.3 (t, 3H)).

Workup

  1. dry with materialdried through azeotrope with toluene

Sources & evidence

ORD record
ord-c1e06c85dd0643a69f2981eaaad8be59
Source dataset
uspto-grants-2011_12
Patent number
US08080666B2

Reaction notes

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