m-Chloroperbenzoic acid → 4-Bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinoline 1-oxide

HRID 1778285Notes

Reaction equation

HRID 1778285 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[CH:10]=2)[N:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:30]>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[CH:10]=2)[N+:5]([O-:30])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 1183239902-((4-Bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole

Product 1

HCID 1183240154-Bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinoline 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-((4-bromoquinolin-6-yl)(4-chlorophenyl)methyl)thiazole (900 mg, 2.165 mmol, 1 equip) and meta-chloroperoxybenzoic acid (578 mg, 3.247 mmol, 1.5 equip) in dichloromethane (30 mL) was stirred at room temperature for 1 h, at which point additional meta-chloroperoxybenzoic acid (578 mg, 3.247 mmol, 1.5 equip) was added and the solution stirred for an additional 3 h. The reaction mixture was washed with 10% Na2CO3 and the aqueous layer extracted with dichloromethane (2×). The combined organic extracts were washed with water, dried over Na2SO4, and concentrated to yield 4-bromo-6-((4-chlorophenyl)(thiazol-2-yl)methyl)quinoline 1-oxide as a pale yellow semi-solid.

Workup

  1. additionwas added
  2. washThe reaction mixture was washed with 10% Na2CO3
  3. extractionthe aqueous layer extracted with dichloromethane (2×)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5a9f87208188446c9bf158a66255a55e
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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