Hydrochloric Acid → HCID 11515798, compound

HRID 502988Notes

Reaction equation

HRID 502988 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.N1C=CC=CC=1.[CH3:14][C:15]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:17]1[N:21]([CH3:22])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[N:19][N:18]=1)[CH3:16].Cl>[Cl-].[Na+].O.C(Cl)(Cl)Cl>[CH3:16][C:15]([N:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:5](=[O:7])[CH3:6])([C:17]1[N:21]([CH3:22])[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH3:29])=[N:19][N:18]=1)[CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68468835HCID 68468835, compound

Product 1

HCID 11515798HCID 11515798, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Acetic anhydride (0.19 ml) and N,N-dimethylaminopyridine (40 mg) were added to a pyridine (10 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 4 days. After the reaction solution and chloroform were added to a 1M hydrochloric acid solution, 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 96:4) and then the resulting solid was washed with ether to obtain 393 mg of N-{1-methyl-1-[4-methyl-5-(2-methylphenyl)-4H-1,2,4-triazol-3-yl]ethyl}-N-phenylacetamide (pale yellow 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 96:4)
  7. washthe resulting solid was washed with ether

Sources & evidence

ORD record
ord-dd248c5b0a404656945655491997443f
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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