N-bromobutanimide → HCID 12781926, compound

HRID 2397594Notes

Reaction equation

HRID 2397594 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[S:13][CH:14]=[CH:15][C:16]=3[CH3:17])=[N:9][C:8]=2[CH:18]=1)([O-:3])=[O:2].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.N(CCCC#N)=NCCCC#N>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]3[S:13][CH:14]=[CH:15][C:16]=3[CH2:17][Br:19])=[N:9][C:8]=2[CH:18]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12781912HCID 12781912, compound

Product 1

HCID 12781926HCID 12781926, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 14151322AzobisbutyronitrileCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 5-nitro-2-(3-methyl-2-thienyl)benzoxazole (11.0 g, 0.042 mole) and N-bromosuccinimide (7.55 g, 0.042 mole) are refluxed for 36 hours in 400 ml of chloroform. Approximately every 12 hours azobisbutyronitrile (0.1 g) is added as a catalyst. The reaction mixture is cooled to room temperature and the precipitated succinimide removed by filtration. The chloroform solution is washed with 150 ml of 5% sodium hydroxide and dried over anhydrous magnesium sulfate. The chloroform is removed under vacuum yielding a solid. Crystallization from ethanol yields 8.6 g of product, melting point 146°-148° C.

Workup

  1. customthe precipitated succinimide removed by filtration
  2. washThe chloroform solution is washed with 150 ml of 5% sodium hydroxide
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe chloroform is removed under vacuum
  5. customyielding a solid
  6. customCrystallization from ethanol

Sources & evidence

ORD record
ord-cdad489a74ea4f819dc5f8fa939e96ab
Source dataset
uspto-grants-1977_05
Patent number
US04022781

Reaction notes

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