Methanol → 2-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid methyl ester

HRID 1733011Notes

Reaction equation

HRID 1733011 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:18]([CH3:22])[C:19]([OH:21])=[O:20])[CH:9]=[CH:10][C:11]=1[N:12]1[CH:16]=[C:15]([Cl:17])[CH:14]=[N:13]1.[CH3:23]O>>[CH3:23][O:20][C:19](=[O:21])[CH:18]([C:8]1[CH:9]=[CH:10][C:11]([N:12]2[CH:16]=[C:15]([Cl:17])[CH:14]=[N:13]2)=[C:6]([Cl:5])[CH:7]=1)[CH3:22]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 203034102-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid

Product 1

HCID 544539792-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid methyl esterYield 86.9%

Procedure

100 ml of thionyl chloride are added to 28.51 g (0.1 mole) of 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid and heated to the boil for half an hour. The solution is concentrated in a vacuum, and 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid chloride is thus obtained. 500 ml of absolute methanol are added; and, again, heating to the boil for half an hour and concentrating are effected, followed by taking up in benzene, washing with water and sodium hydrogen carbonate solution, drying of the organic solution and distilling to produce 26 g (86.9% of theory) of 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid methyl ester (b.p. 126° to 127° C./10-2 mm Hg).

Workup

  1. temperatureheated to the boil for half an hour
  2. concentrationThe solution is concentrated in a vacuum, and 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid chloride
  3. customis thus obtained
  4. temperatureand, again, heating to the boil for half an hour
  5. concentrationconcentrating
  6. washwashing with water and sodium hydrogen carbonate solution
  7. customdrying of the organic solution
  8. distillationdistilling

Sources & evidence

ORD record
ord-c8e733b33a1c4e26aecf9b61e48e7413
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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