Ethyl Acetate → HCID 178443317, compound

HRID 444591Notes

Reaction equation

HRID 444591 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]=[C:12]([NH:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([Cl:25])=[CH:19][C:18]=2[Cl:26])[NH:11]1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH2:34]([S:46]SC(=N)N)[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].C(OCC)(=O)C>C(O)C>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([S:46][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:12]([NH:16][C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([Cl:25])=[CH:19][C:18]=2[Cl:26])=[N:11]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 19865250HCID 19865250, compoundHCID 20567373HCID 20567373, compound

Product 1

HCID 178443317HCID 178443317, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.1 g of 1-(2,4,6-trichlorophenyl)-3-(2,4-dichloro-5-methoxyanilino)-5-pyrazolone was dissolved in 500 ml of 80% ethanol (ratio by volume of ethanol:water=4:1), and 2.5 g of potassium carbonate was added thereto. A solution prepared by dissolving 10.4 g of S-(n-dodecylthio)isothiourea hydrochloride in 100 ml of ethanol was added dropwise thereto over 10 minutes with stirring while heating on a steam bath, and the mixture was stirred for another 10 minutes. After cooled rapidly under a water stream, 300 ml of ethyl acetate was added thereto, and the mixture was washed twice with water. After drying the ethyl acetate layer with anhydrous sodium sulfate, sodium sulfate was removed and the solvent was removed by condensing under a reduced pressure. The residue was crystallized with acetonitrile. The resulting crystals were recrystallized with acetonitrile-ethyl acetate (ratio by volume: 10:1) to obtain 18 g of the coupler having a melting point of 100° to 102° C.

Workup

  1. customA solution prepared
  2. additionwas added dropwise
  3. temperaturewhile heating on a steam bath
  4. stirringthe mixture was stirred for another 10 minutes
  5. additionwas added
  6. washthe mixture was washed twice with water
  7. dry with materialAfter drying the ethyl acetate layer with anhydrous sodium sulfate, sodium sulfate
  8. customwas removed
  9. customthe solvent was removed by condensing under a reduced pressure
  10. customThe residue was crystallized with acetonitrile
  11. customThe resulting crystals were recrystallized with acetonitrile-ethyl acetate (ratio by volume: 10:1)
  12. customto obtain 18 g of the coupler

Sources & evidence

ORD record
ord-a8b3507d40294688af29b9a55f601e36
Source dataset
uspto-grants-1981_04
Patent number
US04264723

Reaction notes

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