Benzonitrile → HCID 59272919, compound

HRID 1409548Notes

Reaction equation

HRID 1409548 reaction equation
[NH2:1][C@@H:2]([CH2:7][OH:8])[CH2:3][CH2:4][S:5][CH3:6].[C:9](#N)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].[Zn+2].[Br-]>[CH3:6][S:5][CH2:4][CH2:3][C@@H:2]1[CH2:7][O:8][C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:1]1

Participants

4

Reactant 2

HCID 7505BenzonitrileHCID 700007387206-44-8

Product 1

HCID 59272919HCID 59272919, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of (R)-methioninol (4.95 g), benzonitrile (8.3 mL) and zinc bromide (250 mg) was stirred at 120° C. for 90 hours under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was washed with water and brine, dried over magnesium sulfate and filtered again. The filtrate was concentrated in vacuo, and the resultant crude product was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1) to give (R)-4-(2-methylthioethyl)-2-phenyl-4,5-dihydrooxazole (3.94 g, yield: 48.6%) as a colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. washthe filtrate was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered again
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe resultant crude product was purified by column chromatography on silica gel (solvent; hexane/ethyl acetate=5/1 to 3/1)

Sources & evidence

ORD record
ord-bfcb7c1b2b8d479aba74eb0bed47add5
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

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