N-bromobutanimide → HCID 20094251, compound

HRID 273743Notes

Reaction equation

HRID 273743 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]3[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])=[N:15][C:14]=2[CH:28]=1>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH2:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]3[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]([O:22][CH3:23])=[O:21])=[N:15][C:14]=2[CH:28]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 20094237Methyl 2-(5-methylbenzoxazol-2-yl)benzoate

Product 1

HCID 20094251HCID 20094251, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (2.35 g) and azo(bisisobutyronitrile) (60 mg) were added to a solution of compound C (3.2 g) in carbon tetrachloride (60 ml). The mixture was heated under reflux for 4 hours and then cooled to ambient temperature. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was recrystallised from hexane to give methyl 2-(5-bromomethyl-benzoxazol-2-yl)benzoate (D) (2.1 g), m.p. 92°-95° C; NMR: 3.9(s, 3H), 4.65(s, 2H), 7.45(dd, 1H), 7.55(dd, 1H), 7.6-7.7(m, 2H), 7.8-7.85(m, 2H), 8.0-8.1(m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customThe residue was recrystallised from hexane

Sources & evidence

ORD record
ord-0f65ea37a79a405892882b27fe8a9fc5
Source dataset
uspto-grants-1995_02
Patent number
US05387592

Reaction notes

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