Water → 2-(4-n-Butylamino-3-nitrophenyl)benzoxazole

HRID 74244Notes

Reaction equation

HRID 74244 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]([NH2:30])[CH2:27][CH2:28][CH3:29].O>C(O)C>[CH2:26]([NH:30][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])[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8007ButylamineHCID 11430Potassium CarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674984732-(4-n-Butylamino-3-nitrophenyl)benzoxazoleYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added potassium carbonate (321 mg, 2.32 mmol) and butylamine (170 mg, 2.32 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 (358 mg, 99.1% 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-acbb5d31bd2d4366817f43cb4db0b9ec
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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