Water → HCID 178443317, compound

HRID 847768Notes

Reaction equation

HRID 847768 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].O>C(O)C.C(OCC)(=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

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19865250HCID 19865250, compoundHCID 20567373HCID 20567373, compound

Product 1

HCID 178443317HCID 178443317, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

15.1 g of 1-(2,4,6-trichlorophenyl)-3-(2,4-dichloro-5-methoxyanilino)-5-pyrazolone was dissolved in 500 cc of 80% ethanol (volume ratio of ethanol to water: 4:1), and 2.5 g of potassium carbonate was added. 10.4 g of S-(n-dodecylthio)isothiourea hydrochloride dissolved in 100 cc of ethanol was dropwise added over a period of 10 minutes on a steam bath with stirring under heating, and further, the mixture was stirred under heating. After cooling with flowing water, 300 cc of ethyl acetate was added, followed by washing twice with water. After drying ethyl acetate layer with anhydrous sodium sulfate, sodium sulfate was removed, the solvent was concentrated under reduced pressure, and the residue was crystallized from acetonitrile. The thus-obtained crystal was recrystallized from acetonitrile-ethyl acetate (volume ratio: 10:1) to obtain 18 g of the coupler having a melting point of 100° to 102° C. (conversion rate: 95%).

Workup

  1. additionwas dropwise added over a period of 10 minutes on a steam bath
  2. temperatureunder heating
  3. stirringfurther, the mixture was stirred
  4. temperatureunder heating
  5. additionwas added
  6. washby washing twice with water
  7. dry with materialAfter drying ethyl acetate layer with anhydrous sodium sulfate, sodium sulfate
  8. customwas removed
  9. concentrationthe solvent was concentrated under reduced pressure
  10. customthe residue was crystallized from acetonitrile
  11. customThe thus-obtained crystal was recrystallized from acetonitrile-ethyl acetate (volume ratio: 10:1)
  12. customto obtain 18 g of the coupler

Sources & evidence

ORD record
ord-da5dacfe1b2c4d08b8e48369d200279c
Source dataset
uspto-grants-1981_10
Patent number
US04293691

Reaction notes

Loading…