N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-1,2,3-triazole-4-carboxamide → 1-{1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazol-4-yl}ethan-1-one

HRID 2074116Notes

Reaction equation

HRID 2074116 reaction equation
CON(C)[C:4]([C:6]1[N:7]=[N:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:10]=1)=[O:5].[CH3:21][Mg]Br>C1COCC1>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:9]2[CH:10]=[C:6]([C:4](=[O:5])[CH3:21])[N:7]=[N:8]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 86617959N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-1,2,3-triazole-4-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 529111011-{1-[(4-methoxyphenyl)methyl]-1H-1,2,3-triazol-4-yl}ethan-1-oneYield 115.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-1-(4-methoxybenzyl)-N-methyl-1H-1,2,3-triazole-4-carboxamide (8.0 g, 0.03 mol) in anhydrous THF (75 mL) was added dropwise methyl magnesium bromide (3.0 M in hexane, 20 mL, 0.058 mol) at 0° C. After the addition, the mixture was stirred at RT overnight. The mixture was quenched with sat. aq. NH4Cl (30 mL) then extracted with CH2Cl2 (3×50 mL). The organics were combined, washed with 1 N aq. NaOH (3×20 mL), water (3×20 mL), brine (50 mL), dried over MgSO4 and evaporated to yield the title compound (8.0 g, 75.0%) as a white solid.

Workup

  1. additionAfter the addition
  2. customThe mixture was quenched with sat. aq. NH4Cl (30 mL)
  3. extractionthen extracted with CH2Cl2 (3×50 mL)
  4. washwashed with 1 N aq. NaOH (3×20 mL), water (3×20 mL), brine (50 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-d2a7f1d66d2d4298b3c9d1980d058c77
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

Loading…