Ammonium Chloride → 5-(5-Isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-thione

HRID 1947185Notes

Reaction equation

HRID 1947185 reaction equation
COC1C=CC([N:9]([C:14](=O)[C:15]2[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[C:18]([O:24][CH2:25][O:26][CH3:27])=[CH:17][C:16]=2[O:28][CH2:29][O:30][CH3:31])[NH:10][C:11]([NH2:13])=[S:12])=CC=1.[Cl-].[NH4+]>[OH-].[Na+]>[CH:21]([C:19]1[C:18]([O:24][CH2:25][O:26][CH3:27])=[CH:17][C:16]([O:28][CH2:29][O:30][CH3:31])=[C:15]([C:14]2[N:13]([C:15]3[CH:20]=[CH:19][C:18]([O:24][CH3:25])=[CH:17][CH:16]=3)[C:11](=[S:12])[NH:10][N:9]=2)[CH:20]=1)([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 866243104-Methoxyphenyl-1-[5-isopropyl-2,4-bis(methoxymethoxy)-benzoyl]thiosemicarbazide

Product 1

HCID 598298385-(5-Isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-thioneYield 171.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4-methoxyphenyl-1-[5-isopropyl-2,4-bis(methoxymethoxy)-benzoyl]thiosemicarbazide (F53-03: 24.9 g, 53.7 mmol) and 5% aqueous sodium hydroxide (500 mL) were placed in a 1 L eggplant shaped flask and heated under reflux for 1 hour. After completing the reaction, the reaction mixture was neutralized with saturated aqueous ammonium chloride, and the solids deposited were collected by filtration, washed with distilled water and then dried under reduced pressure. The crude product thus obtained was purified by suspending in ethyl acetate/hexane and concentrating under reduced pressure to obtain the title compound (F53-04:20.5 g, 85.4%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. customthe reaction
  4. filtrationthe solids deposited were collected by filtration
  5. washwashed with distilled water
  6. customdried under reduced pressure
  7. customThe crude product thus obtained
  8. customwas purified
  9. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-8640c80a99af45dcaafb9806b37f2c0b
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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