Triethylamine → 1-[(4-Methylthiophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone

HRID 1740322Notes

Reaction equation

HRID 1740322 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].[CH3:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([SH:24])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C>[CH3:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][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:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1368964-(Methylsulfanyl)thiophenolHCID 2844936Propanehydrazonoyl chloride, N-(4-methoxyphenyl)-2-oxo-

Product 1

HCID 538001531-[(4-Methylthiophenyl)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 of 4-methylthiothiophenol and 23.4 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-methylthiophenyl)thio]-1-[(4-methoxyphenyl)hydrazono]-2-propanone, mp 124-127° C. 1H NMR(400 MHz, CDCl3): 2.41 (s, 3 H), 2.54 (s, 3 H), 3.78 (s, 3 H), 6.87 (d, J=8.8 Hz, 2 H), 7.12 (m, 6 H), 9.20 (broad s, 1 H).

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-26ab2ceb6c8b43d8828a2532370be23e
Source dataset
uspto-grants-1999_10
Patent number
US05969017

Reaction notes

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