Pyridine → HCID 18937699, compound

HRID 357658Notes

Reaction equation

HRID 357658 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:15]([O:17][C:18]([C:20]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:23]=[N:22][C:21]=1[C:34]([OH:36])=O)=[O:19])[CH3:16].P(Cl)(Cl)(Cl)=O>C(Cl)Cl>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([CH2:25][N:24]2[C:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])=[C:21]([C:34](=[O:36])[N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[N:22]=[N:23]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7515N-MethylanilineHCID 24813Phosphorus oxychlorideHCID 21476203HCID 21476203, compound

Product 1

HCID 18937699HCID 18937699, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-30 °C

Procedure

Under the argon atmosphere, N-methylaniline (0.1 ml, 0.923 mmole) and pyridine (0.32 ml, 3.96 mmole) were added to a solution of 5-ethoxycarbonyl-l-(4-methoxybenzyl)-1,2, 3-triazole-4-carboxylic acid (311 mg, 1.02 mmole) in methylene chloride (3 ml). To the reaction mixture, which had been cooled to -30° C., was added a solution of phosphorus oxychloride (192 mg, 1.25 mmole) in methylene chloride (0.5 ml). After the mixture was stirred at -30° C. for 1 hour, the reaction was quenched by adding water. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with dilute hydrochloric acid, a saturated aqueous sodium hydrogen carbonate and a saturated aqueous saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate =1:1) to give ethyl 1-(4-methoxybenzyl)-4-(N-methyl-N-phenylcarbamoyl)-1,2,3-triazole-5-carboxylate as a yellow crystalline powder (329 mg, 90.4%).

Workup

  1. customthe reaction was quenched
  2. additionby adding water
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with dilute hydrochloric acid
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate =1:1)

Sources & evidence

ORD record
ord-4fe9a3aa2caf4d99849fa807c0669270
Source dataset
uspto-grants-1998_11
Patent number
US05840895

Reaction notes

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