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

HRID 1958321Notes

Reaction equation

HRID 1958321 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([CH3:11])[C:7]=1[C:12]([OH:14])=O)=[O:5])[CH3:2].S(Cl)([Cl:17])=O>>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([CH3:11])[C:7]=1[C:12]([Cl:17])=[O:14])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 60136485Ethyl 5-(chlorocarbonyl)-1-methyl-1H-pyrazole-4-carboxylateYield 110.7%

Procedure

A mixture of 2-methyl-2H-pyrazole-3,4-dicarboxylic acid 4-ethyl ester (6.00 g) and thionyl chloride (82.8 g) was refluxed for 4 h. Excess thionyl chloride was removed under educed pressure; the obtained crude product (7.26 g, assumed purity ˜60%, 66%) was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 4 h
  2. customExcess thionyl chloride was removed

Sources & evidence

ORD record
ord-3d72b5ece5b24cd9bf5f677283063372
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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