m-Chloroperbenzoic acid → 4-[2-(Phenylmethyl)-4-thiazolyl]pyridine-1-oxide

HRID 2309803Notes

Reaction equation

HRID 2309803 reaction equation
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[C:2]1([CH2:1][C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][N+:16]([O-:27])=[CH:17][CH:18]=3)[N:12]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 140969524-(2-Benzyl-1,3-thiazol-4-yl)pyridine

Product 1

HCID 142310544-[2-(Phenylmethyl)-4-thiazolyl]pyridine-1-oxideYield 328%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of n-chloroperbenzoic acid (14.5 g) in dry methylene chloride (150 mL) was added a solution of 2-benzyl-4-(4-pyridyl)thiazole (15.1 g, 0.06 mol) in methylene chloride (125 mL) over thirty minutes. The mixture was allowed to stir overnight at room temperature then an additional portion of m-chloroperbenzoic acid (3.00 g) was added. After an additional six hours of stirring the mixture was extracted with saturated sodium bicarbonate (3×100 mL). The organic layer was dried over sodium sulfate, and concentrated to a total volume of 75 mL. Dilution with ether (200 mL) afforded 4-[2-(phenylmethyl)-4-thiazolyl]pyridine -1-oxide (15.3 g, 95%). Recrystallization from ethanol/ether afforded an analytical sample. mp. 170°-172° C.

Workup

  1. stirringAfter an additional six hours of stirring the mixture
  2. extractionwas extracted with saturated sodium bicarbonate (3×100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to a total volume of 75 mL

Sources & evidence

ORD record
ord-f80843538a39415ab3a3c91b0a471b15
Source dataset
uspto-grants-1987_09
Patent number
US04697012

Reaction notes

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