Sulfuryl chloride → 4-[5-(chloromethyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridine

HRID 732133Notes

Reaction equation

HRID 732133 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH3:6][N:7]1[C:11]([CH3:12])=[N:10][N:9]=[C:8]1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[Cl:4][CH2:12][C:11]1[N:7]([CH3:6])[C:8]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 11600754Pyridine, 4-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)-

Product 1

HCID 589390964-[5-(chloromethyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridineYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Sulfuryl dichloride (0.58 ml, 8.34 mmol) in DCM (8 ml) was slowly added to a cooled (−10° C.) solution of 4-(4,5-dimethyl-4H-1,2,4-triazol-3-yl)pyridine (454 mg, 2.61 mmol) in DCM (25 ml) and DMF (8 ml) and then the solution was stirred for 2 h. NaHCO3 (sat.) was added and the mixture was extracted with EA. The organic phase was dried and concentrated. Recrystallization from EA afforded 124 mg (23%) of the title compound. 1H NMR: 3.83 (s, 3 H) 4.84 (s, 2 H) 7.62 (d, 2 H) 8.82 (d, 2 H).

Workup

  1. extractionthe mixture was extracted with EA
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customRecrystallization from EA

Sources & evidence

ORD record
ord-74e4ce88d0bc44eeacd59a9f3d4cc965
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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