Butyryl chloride → HCID 5199085, compound

HRID 1885102Notes

Reaction equation

HRID 1885102 reaction equation
[C:1]([NH:11][NH2:12])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:13](Cl)(=[O:17])[CH2:14][CH2:15][CH3:16]>N1C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([C:1]([NH:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 767924-Methoxybenzohydrazide

Product 1

HCID 5199085HCID 5199085, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.25 mol of anisohydrazide is dissolved in 300 ml of pyridine. At room temperature, 0.25 mol of butyryl chloride is added dropwise, and the mixture is stirred for a further 11/2 hours. The mixture is subsequently poured into 1.5 1 of ice/water, and the crystals are filtered off with suction and washed with water. The N-(4-methoxybenzoyl)-N'-butyrylhydrazine obtained is recrystallized from toluene. 0.1 mol of this compound and 0.1 mol of Lawesson's reagent are refluxed for 10 hours in 200 ml of THF. 2/3 of the solvent are removed by distillation, the residue is poured into 500 ml of water and 50 ml of 32% sodium hydroxide solution, and the precipitate is filtered off with suction and recrystallized from ethanol/activated charcoal, to give 2-(p-methoxyphenyl)-5-propyl-1,3,4-thiadiazole, m.p. 54°, C 0°.

Workup

  1. filtrationthe crystals are filtered off with suction
  2. washwashed with water

Sources & evidence

ORD record
ord-d93ff309696c450a810ceb4d18f3f27e
Source dataset
uspto-grants-1992_09
Patent number
US05143642

Reaction notes

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