Phosphorus oxychloride → 5-(2-chloropyridin-4-yl)-2-ethyl-4-(3-methylphenyl)-1,3-thiazole

HRID 1727365Notes

Reaction equation

HRID 1727365 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([C:15]2[CH:20]=[CH:19][N+:18]([O-])=[CH:17][CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:7]=1)[CH3:2].C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:19]1[CH:20]=[C:15]([C:5]2[S:4][C:3]([CH2:1][CH3:2])=[N:7][C:6]=2[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[CH:16]=[CH:17][N:18]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 113239374-[2-ETHYL-4-(3-METHYLPHENYL)-1,3-THIAZOL-5-YL]PYRIDINE N-OXIDE

Product 1

HCID 116740635-(2-chloropyridin-4-yl)-2-ethyl-4-(3-methylphenyl)-1,3-thiazoleYield 81%

Procedure

A solution of 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridine N-oxide (1.00 g, 3.37 mmol) in phosphorus oxychloride (6.5 mL) was stirred at 100° C. for 2 hours. The reaction solution was cooled, and poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with brine, then, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1) to obtain a title compound (0.90 g, yield 81%).

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)

Sources & evidence

ORD record
ord-59b9b07b995149358d44d29285c1a15e
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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