Propylamine → HCID 23143269, compound

HRID 732179Notes

Reaction equation

HRID 732179 reaction equation
Cl[C:2]1[O:3][C:4]([CH3:13])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH2:14]([NH2:17])[CH2:15][CH3:16]>C(O)C>[CH3:13][C:4]1[O:3][C:2]([NH:17][CH2:14][CH2:15][CH3:16])=[N:6][C:5]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7852PropylamineHCID 23143330HCID 23143330, compound

Product 1

HCID 23143269HCID 23143269, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chloro-5-methyl-4-phenyl-1,3-oxazole (1.46 g, 7.56 mmol) in ethanol (15 mL) was added propylamine (5 mL), and the mixture was stirred in a sealed tube at 110° C. for 8 hr. The reaction mixture was concentrated and water was added. The mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2:1) to give the title compound (850 mg, yield 52%) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-f62c279acaac4d96a49ec6c22f8f7fd4
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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