2-Methoxy-5-nitroaniline → Carbamic acid, (2-methoxy-5-nitrophenyl)-, phenylmethyl ester

HRID 427610Notes

Reaction equation

HRID 427610 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]>O1CCCC1.O.C(OCC)(=O)C>[CH2:23]([O:22][C:20]([NH:5][C:4]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 74472-Methoxy-5-nitroanilineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 4935662Carbamic acid, (2-methoxy-5-nitrophenyl)-, phenylmethyl esterYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-methoxy-5-nitroaniline (5.0 g, 30 mmol) and potassium carbonate (12 g, 90 mmol) in tetrahydrofuran (200 mL) and water (100 mL) was added benzyl chloroformate (6.1 g, 36 mmol). After 12 h, the mixture was diluted with ethyl acetate (200 mL) and the layers were separated. The organic phase was washed twice with 1 N aqueous hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, twice with saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo. The resulting solid was suspended in diethyl ether and after sonication, the solid was filtered, washed with diethyl ether, and dried in vacuo to give 7.8 g (86%) of the title compound as a light yellow solid.

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed twice with 1 N aqueous hydrochloric acid, once with saturated aqueous sodium chloride solution, twice with saturated aqueous sodium bicarbonate solution, twice with saturated aqueous sodium chloride solution
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customafter sonication
  7. filtrationthe solid was filtered
  8. washwashed with diethyl ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1e055435ee044e48a75ca3c72af4c6a7
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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