Isopropenyl chloroformate → Prop-1-en-2-yl 2-phenyl-4-methylphenylcarbamate

HRID 1930477Notes

Reaction equation

HRID 1930477 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15](Cl)(=[O:20])[O:16][C:17]([CH3:19])=[CH2:18]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[C:1]1([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=2[NH:14][C:15](=[O:20])[O:16][C:17]([CH3:19])=[CH2:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 93846Isopropenyl chloroformateHCID 47121654-Methyl-2-phenylaniline

Product 1

HCID 68982131Prop-1-en-2-yl 2-phenyl-4-methylphenylcarbamateYield 78%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a biphasic solution of 2-phenyl-4-methylbenzenamine (0.29 g, 1.583 mmol) in EtOAc (10 mL) and NaHCO3 (10 ml) was added prop-1-en-2-yl carbonochloridate (0.259 ml, 2.374 mmol) and mixture was stirred for 16 h at RT. The layers were separated and the aqueous layer was extracted with EtOAc (1×30 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to provide prop-1-en-2-yl 2-phenyl-4-methylphenylcarbamate as an off-white solid (0.33 g, 78% yield). 1H NMR (400 MHz, CDCl3): δ 8.00 (brs, 1H), 7.50-7.46 (m, 2H), 7.42-7.35 (m, 3H), 7.18 (dd, J=8.4 Hz, 1.6 Hz, 1H), 7.05 (s, 1H), 6.67 (brs, 1H), 4.72 (s, 1H), 4.68 (s, 1H), 2.34 (s, 3H), 1.94 (s, 3H); MS (ESI) m/z: 290.0 (M+Na+).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (1×30 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a44d71c520e481d9aaaca2631678f45
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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