4-Nitro-m-toluidine → HCID 67125868, compound

HRID 929985Notes

Reaction equation

HRID 929985 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[C:12]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22](=O)[O:23]C2C=CC=CC=2)[CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C>C1COCC1.CN(C1C=CN=CC=1)C>[C:12]([C:16]1[O:20][N:19]=[C:18]([NH:21][C:22]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[CH:3]=2)=[O:23])[CH:17]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 118984-Nitro-m-toluidineHCID 81531DiisopropylethylamineHCID 13489605Phenyl 5-tert-butylisoxazol-3-ylcarbamate

Product 1

HCID 67125868HCID 67125868, compoundYield 164.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-methyl-4-nitroaniline (566 mg, 3.7 mmol) in THF (10 mL) was added phenyl 5-tert-butylisoxazol-3-ylcarbamate (1.0 g, 3.7 mmol), DIEA (972 mL, 5.6 mmol), and DMAP (50 mg, 0.41 mmol). The resulting mixture was refluxed for 60 h. The reaction mixture was then cooled to rt, partitioned between EtOAc (50 mL) and 3N HCl (15 mL). The organic layer was washed with sat. NaHCO3 (15 mL), brine (20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford crude 1-(5-tert-butylisoxazol-3-yl)-3-(3-methyl-4-nitrophenyl)urea (2.0 g, 6.1 mmol). LC-MS (ESI) m/z 319 (M+H)+.

Workup

  1. temperatureThe resulting mixture was refluxed for 60 h
  2. custompartitioned between EtOAc (50 mL) and 3N HCl (15 mL)
  3. washThe organic layer was washed with sat. NaHCO3 (15 mL), brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52154c2c191441c586af96df836e8db0
Source dataset
uspto-grants-2016_03
Patent number
US09296722B2

Reaction notes

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