p-Chlorothiophenol → 1-[(4-Chlorophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone

HRID 323571Notes

Reaction equation

HRID 323571 reaction equation
Cl[C:2](=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[C:3](=[O:5])[CH3:4].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:2](=[N:6][NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:3](=[O:5])[CH3:4])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 8471TriethylamineHCID 2844936Propanehydrazonoyl chloride, N-(4-methoxyphenyl)-2-oxo-

Product 1

HCID 537286961-[(4-Chlorophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 31.7 g (0.139 mol) of 1-chloro-1-[(4-methoxyphenyl)hydrazono]-2-propanone in 400 ml of ethanol was treated with 23.4 g (0.161 mole) of 4-chlorothiophenol followed by 23.4 ml of triethylamine. The suspension was heated at reflux for 2 hours and cooled. The resultant suspension was filtered and the precipitate was washed with 1 portion of cold ethanol. The solids were dried in vacuo to yield 1-[(4-chlorophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone, mp 111.5-113.5° C.

Workup

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 2 hours
  3. temperaturecooled
  4. filtrationThe resultant suspension was filtered
  5. washthe precipitate was washed with 1 portion of cold ethanol
  6. customThe solids were dried in vacuo

Sources & evidence

ORD record
ord-19df923cc5214557a550eec04b170920
Source dataset
uspto-grants-2001_04
Patent number
US06214810B1

Reaction notes

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