4-Isopropoxyaniline → (4-Isopropoxy-phenyl)-carbamic acid 4-nitrophenyl ester

HRID 657183Notes

Reaction equation

HRID 657183 reaction equation
[CH:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14]>C(Cl)Cl.N1C=CC=CC=1>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:13](=[O:14])[NH:9][C:8]2[CH:10]=[CH:11][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 821124-IsopropoxyanilineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 58769998(4-Isopropoxy-phenyl)-carbamic acid 4-nitrophenyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-isopropoxyaniline (9.06 g, 60.0 mmol) in DCM (120 mL) and pyridine (30 mL) was added 4-nitrophenyl chloroformate (10.9 g, 54.0 mmol) portionwise with stirring over ˜1 min with brief ice-bath cooling. After stirring at rt for 1 h, the homogeneous solution was diluted with DCM (300 mL) and washed with 0.6 M HCl (1×750 mL) and 0.025 M HCl (1×1 L). The organic layer was dried (Na2SO4) and concentrated to give the title compound as a light violet-white solid (16.64 g, 98%). 1H-NMR (300 MHz, CDCl3) δ 8.26 (m, 2H), 7.40-7.28 (m, 4H), 6.98 (br s, 1H), 6.87 (m, 2H), 4.50 (heptet, J=6.0 Hz, 1H), 1.33 (d, J=6.0 Hz, 6H). LC/MS (ESI): calcd mass 316.1, found 633.2 (2 MH)+.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at rt for 1 h
  3. washwashed with 0.6 M HCl (1×750 mL) and 0.025 M HCl (1×1 L)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2d31ce3cd3224268a1cfc4ef5b16c582
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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