Ethanol → HCID 178470496, compound

HRID 1169911Notes

Reaction equation

HRID 1169911 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-51be6480fe4347718bf9d00b0679cf5b
Source dataset
uspto-grants-2010_11
Patent number
US07825140B2

Reaction notes

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