Water → HCID 15429393, compound

HRID 725269Notes

Reaction equation

HRID 725269 reaction equation
CS[C:3]([S:13][CH3:14])=[C:4]([C:10](=O)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[C:17]=1[NH:24][NH2:25].O>C(O)C>[CH2:8]([O:7][C:5]([C:4]1[C:3]([S:13][CH3:14])=[N:25][N:24]([C:17]2[C:18]([Cl:23])=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[Cl:15])[C:10]=1[CH3:11])=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 4997384Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl ester

Product 1

HCID 15429393HCID 15429393, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.22 g (5.23 mmol) of ethyl 3,3-bismethylthio-2-acetylacrylate and 1.11 g (5.23 mmol) of 2,4,6-trichlorophenylhydrazine in 12 mL of ethanol was heated at reflux for 2 hours. The cooled reaction mixture was then poured into cold water and the product was extracted into ether. The ethereal extracts were dried and evaporated and the residues were chromatographed on silica gel using 6:1 hexane/ethyl acetate as eluent to give 1.12 g (56%) of the desired product as a crystalline solid, m.p. 95°-98° C. 1H-NMR (CDCl3) δ1.38 (3H, t, J=7), 2.30 (3H, s), 2.49 (3H, s.), 4.31 (2H, q, J=7), 7.47 m(2H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe cooled reaction mixture
  4. extractionthe product was extracted into ether
  5. customThe ethereal extracts were dried
  6. customevaporated
  7. customthe residues were chromatographed on silica gel using 6:1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-6e8453bf8a944c2784dbe3f4a925d266
Source dataset
uspto-grants-1998_01
Patent number
US05705646

Reaction notes

Loading…