Water → HCID 66966094, compound

HRID 1514849Notes

Reaction equation

HRID 1514849 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[NH2:11])([O-:3])=[O:2].C([O-])(O)=O.[Na+].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].O>C(#N)C.ClCCl>[CH2:21]([O:20][C:18](=[O:19])[NH:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([NH2:11])[CH:6]=1)[CH3:22]

Participants

7

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 212084-Nitro-1,3-benzenediamineHCID 516892Sodium Bicarbonate

Product 1

HCID 66966094HCID 66966094, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-nitro-benzene-1,3-diamine (1.6 g) in acetonitrile (20 mL) was added NaHCO3 (1 g) and ethyl chloroformate (1.0 mL). The mixture was heated at 75° C. with stirring overnight. Cooled to ambient temperature, the mixture was diluted by water and extracted twice with ethyl acetate. Combined organics were dried over Na2SO4, filtered, and concentrated to give crude yellow solid. Trituration from dichloromethane afforded (3-amino-4-nitro-phenyl)-carbamic acid ethyl ester: 1H NMR (400 MHz, CD3OD) 7.9 (d, 1H), 7.3 (s, 1H), 6.5 (d, 1H), 4.2 (q, 2H), 1.3 (t, 3H).

Workup

  1. temperatureCooled to ambient temperature
  2. extractionextracted twice with ethyl acetate
  3. dry with materialCombined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude yellow solid

Sources & evidence

ORD record
ord-e9a06b9ee9aa4e48858463d4e7987f0f
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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