N-bromobutanimide → HCID 22118335, compound

HRID 1274856Notes

Reaction equation

HRID 1274856 reaction equation
[CH3:1][C:2]1[O:7][CH2:6][N:5]([C:8]([CH3:18])([CH3:17])[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4](=[O:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Br:26]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:26][CH:10]([C:9](=[O:16])[C:8]([N:5]1[C:4](=[O:19])[C:3]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:2]([CH3:1])[O:7][CH2:6]1)([CH3:17])[CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22118254Ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate

Product 1

HCID 22118335HCID 22118335, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of ethyl 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate (500 mg), N-bromosuccinimide(258 mg) and benzoyl peroxide (10 mg) was refluxed under a lamp whilst stirring in benzene for 10 minutes. After cooling, the solid was filtered, the filtrate evaporated and the residue purified by column chromatography (hexane/ethyl acetate 4:1) to give ethyl 2-bromo-4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-1,3-oxazin-3-yl)-4-methyl-3-oxo-pentanoate (Compound 190, 400 mg ) as a yellow gum, NMR 1.21(t,3H), 1.55(d,6H), 1.94(s,3H), 4.15(q,2H), 5.23(s,1H), 5.26(d--d,2H) and 7.21-7.37(m,5H).

Workup

  1. temperaturewas refluxed under a lamp
  2. temperatureAfter cooling
  3. filtrationthe solid was filtered
  4. customthe filtrate evaporated
  5. customthe residue purified by column chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-8b95c559730b4a398d5e8223da635608
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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