Water → HCID 9948405, compound

HRID 2121623Notes

Reaction equation

HRID 2121623 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][O:10][C:11]=2[C:12]2[CH:13]=[CH:14][C:15]([NH:18][NH:19][C:20](=O)[CH:21]([CH3:23])[CH3:22])=[N:16][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Na+]>P(Cl)(Cl)(Cl)=O>[CH:21]([C:20]1[N:16]2[CH:17]=[C:12]([C:11]3[O:10][CH:9]=[N:8][C:7]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:13]=[CH:14][C:15]2=[N:18][N:19]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 69561320HCID 69561320, compound

Product 1

HCID 9948405HCID 9948405, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
75 °C

Procedure

Isobutyric acid N′-[5-(4-phenyl-oxazol-5-yl)-pyridin-2-yl]-hydrazide (730 mg, 2.26 mmol) was taken up in phosphorous oxychloride (10 mL) and heated at 75° C. for 18 hours. The reaction was cooled with an ice bath, added to a beaker of water (50 mL), and the mixture was made basic by dropwise addition with 3 N sodium hydroxide. The basic mixture was extracted with ethyl acetate (3×); the combined organic layers were washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo to a yellow oil. The residue was recrystallized from ethyl acetate/methanol (95/5) affording the title compound as yellow crystals (294 mg, 43%). The filtrate was purified by flash chromatography (eluting with ethyl acetate/methanol 97:3) to give more of the title compound (220 mg, 32%). LCMS (m/z) 305 M+1. 1H NMR (400 MHz, CDCl3) δ8.22 (s 1 H), 8.05 (s, 1 H), 7.84 (d, 1 H, J=9.8 Hz), 7.64-7.66 (m, 2 H), 7.44 7.49 (m, 4 H), 3.29-3.34 (m, 1 H), 1.51 (d, 6 H, J=7.2 Hz).

Workup

  1. temperatureThe reaction was cooled with an ice bath
  2. extractionThe basic mixture was extracted with ethyl acetate (3×)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo to a yellow oil
  7. customThe residue was recrystallized from ethyl acetate/methanol (95/5)

Sources & evidence

ORD record
ord-357589d63be244ffb5a03d1f8524a502
Source dataset
uspto-grants-2004_02
Patent number
US06696464B2

Reaction notes

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