Thionyl Chloride → HCID 53978393, compound

HRID 2398614Notes

Reaction equation

HRID 2398614 reaction equation
O[CH2:2][N:3]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[C:5]([Cl:12])=[N:4]1.S(Cl)([Cl:15])=O>>[Cl:12][C:5]1[C:6]([N+:9]([O-:11])=[O:10])=[C:7]([CH3:8])[N:3]([CH2:2][Cl:15])[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21433351HCID 21433351, compound

Product 1

HCID 53978393HCID 53978393, compound

Procedure

A mixture of 13.58 g (0.0708 mole) 1-hydroxymethyl-3-chloro-5-methyl-4-nitropyrazole and 30 ml of thionyl chloride was heated under reflux overnight and concentrated in vacuo. Benzene was added and the solution was concentrated again. This was replicated two more times. This left 15.8 g of an amber liquid. This was distilled at 155°-170° (air bath temperature)/1.25 mm to obtain a colorless liquid which crystallized upon standing. Recrystallization from benzene-Skelly B solvent gave 9.52 g of white crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. concentrationconcentrated in vacuo
  4. additionBenzene was added
  5. concentrationthe solution was concentrated again
  6. distillationThis was distilled at 155°-170° (air bath temperature)/1.25 mm
  7. customto obtain a colorless liquid which
  8. customcrystallized
  9. customRecrystallization from benzene-Skelly B solvent

Sources & evidence

ORD record
ord-b3a04865b32548849e17e62feddf142b
Source dataset
uspto-grants-1977_05
Patent number
US04025530

Reaction notes

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