Hydrochloric Acid → HCID 68470278, compound

HRID 502987Notes

Reaction equation

HRID 502987 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:16][C:17]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:19]1[N:23]([CH3:24])[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])=[N:21][N:20]=1)[CH3:18].Cl>[Cl-].[Na+].O.C(Cl)(Cl)Cl>[CH3:18][C:17]([N:32]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:19]1[N:23]([CH3:24])[C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])=[N:21][N:20]=1)[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 68468835HCID 68468835, compound

Product 1

HCID 68470278HCID 68470278, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Benzoyl chloride (0.21 ml) and N,N-dimethylaminopyridine (40 mg) were added to a pyridine (15 ml) solution of N-{1-methyl-1-[4-methyl-5-(2-methylphenyl)-4H-1,2,4-triazol-3-yl]ethyl}aniline (500 mg), followed by stirring at 80° C. for 3 days. After the reaction solution and chloroform were added to 1M hydrochloric acid, the reaction solution and chloroform were added to brine and then the organic layer was separated. Furthermore, the organic layer washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution successively, dried over anhydrous magnesium-sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=99:1 to 98:2) and then the resulting solid washed with ether to obtain 523 mg of N-{1-methyl-1-[4-methyl-5-(2-methylphenyl)-4H-1,2,4-triazol-3-yl]ethyl}-N-phenylbenzamide (colorless solid).

Workup

  1. customthe organic layer was separated
  2. washFurthermore, the organic layer washed with a saturated aqueous sodium hydrogen carbonate solution
  3. dry with materiala saturated sodium chloride solution successively, dried over anhydrous magnesium-sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=99:1 to 98:2)
  7. washthe resulting solid washed with ether

Sources & evidence

ORD record
ord-21105205039b46c1850aaa33d0f11ff0
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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