Sodium Chloride → {3-[5-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-propyl}-dimethylamine

HRID 1947225Notes

Reaction equation

HRID 1947225 reaction equation
[CH:1]([C:4]1[C:5]([O:28][CH2:29][O:30][CH3:31])=[CH:6][C:7]([O:24][CH2:25][O:26][CH3:27])=[C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:12](=[S:15])[NH:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:39][N:40]([CH3:45])[CH2:41][CH2:42][CH2:43]Cl.[Cl-].[Na+]>CN(C)C=O>[CH:1]([C:4]1[C:5]([O:28][CH2:29][O:30][CH3:31])=[CH:6][C:7]([O:24][CH2:25][O:26][CH3:27])=[C:8]([C:10]2[N:11]([C:16]3[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=3)[C:12]([S:15][CH2:43][CH2:42][CH2:41][N:40]([CH3:45])[CH3:39])=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 598298385-(5-Isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-thione

Product 1

HCID 59829887{3-[5-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-4H-[1,2,4]triazol-3-ylsulfanyl]-propyl}-dimethylamineYield 121.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-(4-methoxy-phenyl)-2,4-dihydro-[1,2,4]triazol-3-thione (F53-04: 3.5 g, 7.9 mmol), potassium carbonate (2.6 g, 18.9 mmol) and dimethylformamide (150 mL) were placed in a 500 mL eggplant shaped flask, and then 3-dimethylaminopropyl chloride hydrochloride (1.49 g, 9.4 mmol) was added, and the mixture was stirred at 100° C. for 2 hours. A similar operation was carried out using the same amount of materials, and after the reaction was completed, the mixture was cooled, mixed with saturated sodium chloride solution (700 mL) and extracted twice with ethyl acetate. The organic layers were combined, washed 4 times with saturated sodium chloride solution (500 mL), dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol) to obtain the title compound (F68-01: 5.1 g, 61%).

Workup

  1. temperaturethe mixture was cooled
  2. extractionextracted twice with ethyl acetate
  3. washwashed 4 times with saturated sodium chloride solution (500 mL)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-fc243ae0288d4da49e95b64f35a6fb86
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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