m-Chloroperbenzoic acid → HCID 13749938, compound

HRID 1789336Notes

Reaction equation

HRID 1789336 reaction equation
[CH3:1][C:2]1[C:3]([CH2:17][S:18][C:19]2[NH:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12].ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:17][S:18]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)=[O:36])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:16])([F:15])[C:11]([F:12])([F:14])[F:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13654767HCID 13654767, compound

Product 1

HCID 13749938HCID 13749938, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2-[3-methyl-4-(2,2,3,3,3-pentafluoropropoxy)pyrid-2-yl]methylthiobenzimidazole (2.2 g) in chloroform (20 ml) was added dropwise under ice-cooling over a period of 30 minutes m-chloroperbenzoic acid (1.3 g) dissolved in chloroform (15 ml). The solution was washed with a saturated aqueous solution of sodium hydrogen carbonate, then dried on magnesium sulfate, and concentrated. The residue was chromatographed on a column of silica gel (50 g), eluted with ethyl acetate, and then recrystallized from acetone-isopropyl ether to give 1.78 g of 2-[3-methyl-4-(2,2,3,3,3-pentafluoropropoxy)pyrid-2-yl]methylsulfinylbenzimidazole as pale yellow prisms, m.p. 161°-163° C. (decomp.).

Workup

  1. washThe solution was washed with a saturated aqueous solution of sodium hydrogen carbonate
  2. customdried on magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on a column of silica gel (50 g)
  5. washeluted with ethyl acetate
  6. customrecrystallized from acetone-isopropyl ether

Sources & evidence

ORD record
ord-476b763d978042baa4c140cbda1fb6b6
Source dataset
uspto-grants-1987_08
Patent number
US04689333

Reaction notes

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