m-Chloroperbenzoic acid → HCID 10293318, compound

HRID 1816674Notes

Reaction equation

HRID 1816674 reaction equation
[F:1][C:2]([F:25])([F:24])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH:8]=1.ClC1C=CC=C(C(OO)=[O:34])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:25][C:2]([F:24])([F:1])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14]([C:15]2[NH:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[O:34])[CH:8]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22493631HCID 22493631, compound

Product 1

HCID 10293318HCID 10293318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The thus-obtained 2-[4-(4,4,4-trifluorobutoxy)pyridin-2-yl-methylthio]-1H-benzimidazole (1.27 g) was dissolved in methylene chloride (20 mL). A solution of 80% m-chloroperbenzoic acid (746 mg) in methylene chloride (10 mL) was added dropwise at −30° C., and the mixture was stirred for an hour at the same temperature. A saturated sodium bicarbonate solution (30 mL) was added to the reaction mixture. The temperature of the mixture was returned to room temperature, and the mixture was stirred for 10 minutes, followed by extraction with methylene chloride. The organic layer was washed sequentially with water and brine, and brought to dryness over sodium sulfate anhydrate. The solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography (silica gel: NH-DM1020 (product of Fuji Silicia), chloroform:methanol=10:1), whereby 2-[4-(4,4,4-trifluorobutoxy)pyridin-2-yl-methanesulfinyl]-1H-benzimidazole was obtained (1.2 g).

Workup

  1. customwas returned to room temperature
  2. stirringthe mixture was stirred for 10 minutes
  3. extractionfollowed by extraction with methylene chloride
  4. washThe organic layer was washed sequentially with water and brine
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-db42d1f187c34f5db8c1eab4cdcd7613
Source dataset
uspto-grants-2005_04
Patent number
US06884810B2

Reaction notes

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