Pyridine → 2-(4-Methoxybenzoyl)-2-(4-methoxyphenyl)hydrazinecarbothioamide

HRID 584731Notes

Reaction equation

HRID 584731 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:11](=[S:13])[NH2:12])=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.N1C=CC=CC=1>>[CH3:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[NH:10][C:11](=[S:13])[NH2:12])=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7477p-Anisoyl chlorideHCID 28261724-Methoxyphenylthiosemicarbazide

Product 1

HCID 223415752-(4-Methoxybenzoyl)-2-(4-methoxyphenyl)hydrazinecarbothioamideYield 33%

Procedure

A mixture of 2-(4-methoxyphenyl)hydrazinecarbothioamide (0.5 g, 2.53 mmol), 4-methoxybenzoyl chloride (541 mg, 3.17 mmol), and pyridine (0.256 mL, 3.17 mmol) intoluene (10 mL) was refluxed for 1 hour. After cooling, the solvent was removed under reduced pressure. diisopropyl ether and small amount of methanol was added to the residue and a generated precipitate was isolated by filtration, washed with methanol-diisopropyl ether, and dried in vacuo to give 2-(4-methoxybenzoyl)-2-(4-methoxyphenyl)hydrazinecarbothioamide (277 mg, 33% yield).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure
  4. additiondiisopropyl ether and small amount of methanol was added to the residue
  5. customa generated precipitate was isolated by filtration
  6. washwashed with methanol-diisopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-705c820ea4f24b96b6acafc6a0823867
Source dataset
uspto-grants-2005_08
Patent number
US06927230B2

Reaction notes

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