Water → 2-(2-(4-Methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole

HRID 74297

Reaction equation

HRID 74297 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(N(CC)CC)C.Cl.[C:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1)([O:30][CH3:31])=[O:29].O>C(#N)C>[CH3:31][O:30][C:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:37][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])=[CH:34][CH:33]=1)=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674984512-(2-(4-Methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazoleYield 95.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (250 mg, 0.968 mmol) in acetonitrile (5 mL) was added triethylamine (245 mg, 2.42 mmol) and 4-carbomethoxybenzylamine hydrochloride (215 mg, 1.07 mmol), and this was heated to reflux for 2 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 (372 mg, 95% yield).

Workup

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

Sources & evidence

ORD record
ord-4edf92dcebf1480ca969c2aa9d0f382b
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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