4-Isopropylaniline → (4-Isopropylphenyl)-carbamic acid 4-nitrophenyl ester

HRID 657190Notes

Reaction equation

HRID 657190 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:13]>C(Cl)Cl.N1C=CC=CC=1>[N+:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][C:12](=[O:13])[NH:8][C:7]2[CH:9]=[CH:10][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)=[CH:20][CH:19]=1)([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 74644-IsopropylanilineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 46186565(4-Isopropylphenyl)-carbamic acid 4-nitrophenyl esterYield 95.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-isopropylaniline (3.02 g, 22.3 mmol) in DCM (40 mL) and pyridine (10 mL) was added 4-nitrophenyl chloroformate (4.09 g, 20.3 mmol) portionwise with stirring over ˜30 sec with brief ice-bath cooling. After stirring at rt for 1 h, the homogeneous solution was diluted with DCM (100 mL) and washed with 0.6 M HCl (1×250 mL), 0.025 M HCl (1×400 mL), water (1×100 mL), and 1 M NaHCO3 (1×100 mL). The organic layer was dried (Na2SO4) and concentrated to give the title compound as a light peach-colored solid (5.80 g, 95%). 1H-NMR (300 MHz, CDCl3) δ 8.28 (m, 2H), 7.42-7.32 (m, 4H), 7.22 (m, 2H), 6.93 (br s, 1H), 2.90 (h, J=6.9 Hz, 1H), 1.24 (d, J=6.9 Hz, 6H). LC/MS (ESI): calcd mass 300.1, 601.3 (2MH)+.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at rt for 1 h
  3. washwashed with 0.6 M HCl (1×250 mL), 0.025 M HCl (1×400 mL), water (1×100 mL), and 1 M NaHCO3 (1×100 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7483340261244786bce52d53606ceb87
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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