Ammonium Chloride → (1,2-Dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 926559Notes

Reaction equation

HRID 926559 reaction equation
Br[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=1.C([Li])CCC.CON(C)[C:17]([C:19]1[N:23]([CH3:24])[N:22]=[N:21][CH:20]=1)=[O:18].[Cl-].[NH4+]>O1CCCC1>[CH3:7][N:6]1[C:2]([C:17]([C:19]2[N:23]([CH3:24])[N:22]=[N:21][CH:20]=2)=[O:18])=[CH:3][N:4]=[C:5]1[CH3:8]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 72048795-bromo-1,2-dimethyl-1H-imidazoleHCID 86715652N-Methoxy-N,1-dimethyl-1H-1,2,3-triazole-5-carboxamideHCID 178418339Butyllithium

Product 1

HCID 118006222(1,2-Dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-1,2-dimethyl-1H-imidazole (1.5 g, 7.54 mmol) in tetrahydrofuran (25 mL) was cooled to −66° C. Maintaining a temperature of <−50° C., n-butyllithium (3.2 mL, 2.5 M in hexanes, 8.3 mmol) was added over 5 minutes. The reaction mixture was stirred for 15 minutes and then a solution of N-methoxy-N,1-dimethyl-1H-1,2,3-triazole-5-carboxamide (1.3 g, 7.54 mmol, Intermediate 77: step a) in tetrahydrofuran (3 mL) was added over 3 minutes. The mixture was allowed to warm to room temperature while stirring over 30 minutes. Half-saturated aqueous ammonium chloride solution (40 mL) was added and the layers were mixed and separated. The aqueous layer was extracted twice with tetrahydrofuran (50 mL) and then with dichloromethane (50 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to dryness. The material was triturated with isopropyl alcohol (29 mL), filtered, and rinsed twice with hexanes (25 mL) providing the title compound as a white solid.

Workup

  1. additionwas added over 5 minutes
  2. stirringwhile stirring over 30 minutes
  3. additionthe layers were mixed
  4. customseparated
  5. extractionThe aqueous layer was extracted twice with tetrahydrofuran (50 mL)
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe material was triturated with isopropyl alcohol (29 mL)
  10. filtrationfiltered
  11. washrinsed twice with hexanes (25 mL)

Sources & evidence

ORD record
ord-16b71833b4414229bbdeb5b4ea5b5c06
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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