N-bromobutanimide → Methyl 5-methyl-2-(4-nitrophenyl)oxazole-4-carboxylate

HRID 43576Notes

Reaction equation

HRID 43576 reaction equation
[CH3:1][CH:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[N:4][CH:3]1[C:16]([O:18][CH3:19])=[O:17].BrN1C(=O)CCC1=O>C1C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67548873Methyl 5-methyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate

Product 1

HCID 67548650Methyl 5-methyl-2-(4-nitrophenyl)oxazole-4-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The same operation as in Example (96a) was performed using methyl 5-methyl-2-(4-nitrophenyl)-4,5-dihydro-1,3-oxazole-4-carboxylate obtained in Example (97b) (1.1 g, 4.16 mmol), α,α-bisisobutyronitrile (33 mg, 0.2 mmol), N-bromosuccinimide (0.78 g, 4.37 mmol) and benzene (20 mL). Purification by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1) gave 0.75 g of the title compound as a light yellow solid (69%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/4, 1/2, 1/1, 2/1)

Sources & evidence

ORD record
ord-48b654662c5545c68a9464c7f368f63d
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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