Acetic Acid → HCID 23725964, compound

HRID 2219331Notes

Reaction equation

HRID 2219331 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8][O:9][C:10]=2[CH3:11])[N:3]=[CH:2]1.[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C>CN(C=O)C>[CH2:20]([N:1]1[CH:5]=[C:4]([C:6]2[C:7]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[N:8][O:9][C:10]=2[CH3:11])[N:3]=[CH:2]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178434980HCID 178434980, compound

Product 1

HCID 23725964HCID 23725964, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4-(1H-imidazol-4-yl)-5-methyl-3-phenyl-isoxazole (100 mg, 0.44 mmol) in DMF (2 mL) was added over 10 min to a suspension of NaH (20 mg, 0.47 mmol) in DMF (1 mL) at room temperature and after 30 min benzyl bromide (83.5 mg, 0.49 mmol) was added. After 2 h at room temperature, the mixture was poured into aqueous acetic acid (10%) and extracted with ethyl acetate. The organic extracts were then washed with water and brine, and then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:1) afforded the title compound (88 mg, 63%) which was obtained as a colourless gum. MS: m/e=316.1 [M+H]+.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were then washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ca360e57e5984c58be38026382908c0c
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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