Thionyl Chloride → Ethyl 5-(chlorocarbonyl)-1-methyl-1H-pyrazole-4-carboxylate

HRID 908215Notes

Reaction equation

HRID 908215 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([CH2:11]C)[C:7]=1[C:13]([OH:15])=O)=[O:5])[CH3:2].S(Cl)([Cl:18])=O>>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([CH3:11])[C:7]=1[C:13]([Cl:18])=[O:15])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 670418082-Ethyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester

Product 1

HCID 60136485Ethyl 5-(chlorocarbonyl)-1-methyl-1H-pyrazole-4-carboxylate

Procedure

A mixture of 2-ethyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester (Example 10, steps 1-3, 3 g, 15 mmol) and thionyl chloride (40 ml) was heated to reflux (4 h). The thionyl chloride was evaporated, and the residue (3.38 g, 64%) was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux (4 h)
  3. customThe thionyl chloride was evaporated
  4. customthe residue (3.38 g, 64%) was used in the next step without further purification

Sources & evidence

ORD record
ord-a22c390fdd9849deb0b38aeed7aabaa8
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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