Water → 2-(4-Neopentylamino-3-nitrophenyl)benzoxazole

HRID 74256

Reaction equation

HRID 74256 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].[CH2:26]([NH2:31])[C:27]([CH3:30])([CH3:29])[CH3:28].O>C(O)C>[CH2:26]([NH:31][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18])[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79882NeopentylamineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674990142-(4-Neopentylamino-3-nitrophenyl)benzoxazoleYield 97.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (200 mg, 0.774 mmol) in ethanol (5 mL) was added potassium carbonate (214 mg, 1.55 mmol) and neopentylamine (135 mg, 1.55 mmol), and this was heated to reflux for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and after the precipitated crystals were filtered and washed with water, they were dried to yield the title compound (245 mg, 97% yield).

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 4 hours
  3. filtrationafter the precipitated crystals were filtered
  4. washwashed with water, they
  5. customwere dried

Sources & evidence

ORD record
ord-6cd0155b2f8b4c6da92d942606137c28
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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