Sodium Carbonate → 5-Difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulphinyl]-4,6-dimethyl-1H-benzimidazole

HRID 1789042Notes

Reaction equation

HRID 1789042 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][CH:13]([F:38])[O:14][C:15]1[C:35]([CH3:36])=[CH:34][C:18]2[NH:19][C:20]([S:22][CH2:23][C:24]3[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][N:25]=3)=[N:21][C:17]=2[C:16]=1[CH3:37].C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[F:38][CH:13]([F:12])[O:14][C:15]1[C:35]([CH3:36])=[CH:34][C:18]2[NH:19][C:20]([S:22]([CH2:23][C:24]3[C:29]([O:30][CH3:31])=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][N:25]=3)=[O:6])=[N:21][C:17]=2[C:16]=1[CH3:37]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 201895845-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylthio]-4,6-dimethyl-1H-benzimidazole

Product 1

HCID 201895315-Difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulphinyl]-4,6-dimethyl-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

5 ml of a 0.2N solution of m-chloroperoxybenzoic acid in methylene chloride are added dropwise at -40° C. to a solution of 0.39 g (1 mmol) of 5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylthio]-4,6-dimethyl-1H-benzimidazole in 20 ml of methylene chloride, and the mixture is stirred for 15 minutes. 0.5 ml of triethylamine are then added and the reaction mixture is poured into 20 ml of a 1:1 mixture of 5% sodium carbonate solution and 5% sodium thiosulphate solution. After phase separation, the aqueous phase is extracted twice more with 30 ml of methylene chloride each time, and the combined organic phases are washed with sodium carbonate solution, dried over magnesium sulphate, filtered and concentrated to 2 ml. After crystallisation from diisopropyl ether, the crystals are filtered off and dried to constant weight. This gives 0.3 g (74% of theory) of the title compound as a colourless solid of m.p. 163°-164° C. (decomposition).

Workup

  1. customAfter phase separation
  2. extractionthe aqueous phase is extracted twice more with 30 ml of methylene chloride each time
  3. washthe combined organic phases are washed with sodium carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to 2 ml
  7. customAfter crystallisation from diisopropyl ether
  8. filtrationthe crystals are filtered off
  9. customdried to constant weight

Sources & evidence

ORD record
ord-2e260586ca2f47d4818b96183895a114
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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