2-(Chloromethyl)-4-methoxy-3,5-dimethylpyridine → HCID 86745701, compound

HRID 1030574Notes

Reaction equation

HRID 1030574 reaction equation
[CH3:1]/[C:2](/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3]\[CH2:4][S:5][C:6]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]=1.[CH3:21][C:22]1[C:23]([CH2:31]Cl)=[N:24][CH:25]=[C:26]([CH3:30])[C:27]=1[O:28][CH3:29]>CN(C)C=O.C(Cl)Cl>[CH3:21][C:22]1[C:23]([CH2:31][N:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=[C:6]2[S:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[N:24][CH:25]=[C:26]([CH3:30])[C:27]=1[O:28][CH3:29]

Participants

5

Reactant 2

HCID 8199922-(Chloromethyl)-4-methoxy-3,5-dimethylpyridineHCID 67916129HCID 67916129, compound

Product 1

HCID 86745701HCID 86745701, compoundYield 126.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(3,7-dimethyl-2,6(E)-octadienyl)thio]-1H-1,3-benzimidazole from Example 1 (1.5 g, 5.2 mmol) and 3,5-dimethyl-4-methoxy-2-pyridylmethyl chloride (0.465 g, 5 2 mmol) in dimethylformamide (7 mL) at 0° C. under nitrogen was added dropwise triton-B (5 mL of a 40% solution). The solution was stirred at ambient temperature for 72 hours, then at 50° C. for 48 hours. Evaporation of the solvent gave a residue which was dissolved in CH2Cl2, washed with water and dried over Na2SO4. Evaporation of the solvent and flash chromatography of the resultant oil (10% Et2O/CH2Cl2, Merck Kieselgel) gave 1.1 g of 1-(3,5-dimethyl-4-methoxy-2-pyridylmethyl)-2-[(3,7-dimethyl-2,6(E)-octadienyl)thio]-1H-1,3-benzimidazole (free base) which was converted to its oxalate salt (1.36 g). m.p. 76°-80° C. NMR (DMSO-d6) δ7.93(s,1H), 7.5(m,1H), 7.1(m,3H), 5.4(s,2H), 5.37(m,1H), 5.07(m,1H), 3.93(m,2H), 3.70(s,3H), 2,27(s,3H), 2.15(s,3H), 2.0(m,4H), 1.6(s,3H), 1.53(s,3H), 1.07(s,3H).

Workup

  1. waitat 50° C. for 48 hours
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. washwashed with water
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent and flash chromatography of the resultant oil (10% Et2O/CH2Cl2, Merck Kieselgel)

Sources & evidence

ORD record
ord-0ca63c93e0ab4e03a73eb5e4c3578843
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

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