P-Phenylenediamine → tert-Butyl (4-aminophenyl)carbamate

HRID 1717245Notes

Reaction equation

HRID 1717245 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.C(N(CC)CC)C.[C:16](=O)([O:22]C(C)(C)C)[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C.C(OCC)(=O)C>[NH2:7][C:6]1[CH:5]=[CH:4][C:3]([NH:8][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:2][CH:1]=1

Participants

6

Reactant 3

HCID 7814P-PhenylenediamineHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 688611tert-Butyl (4-aminophenyl)carbamateYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of p-phenylenediamine (16.2 g) and triethylamine (20.8 ml) in DMF (80 ml) was added di-tert-butyl carbonate (34.4 ml). The reaction mixture was stirred at room temperature for 8 hr and diluted with ethyl acetate. The ethyl acetate solution was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=4/1 to ethyl acetate), and the resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (29.2 g, 95%).

Workup

  1. washThe ethyl acetate solution was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column (hexane/ethyl acetate=4/1 to ethyl acetate)
  5. customthe resultant product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d236603ea5f14a378a81206a8c4dd221
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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