Styrene → HCID 16719385, compound

HRID 1767268Notes

Reaction equation

HRID 1767268 reaction equation
[C:1](=[O:5])([O:3][CH3:4])[NH2:2].[C:6](Cl)(=[O:10])[CH:7]=[CH:8][CH3:9].C=CC1C=CC=CC=1>C(Cl)Cl.Cl[Cu]>[C:6]([NH:2][C:1](=[O:5])[O:3][CH3:4])(=[O:10])/[CH:7]=[CH:8]/[CH3:9]

Participants

6

Reactant 3

HCID 7501StyreneHCID 11722Methyl CarbamateHCID 790802-Butenoyl chloride

Product 1

HCID 16719385HCID 16719385, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
114 °C

Procedure

To a mixture of methyl carbamate (1.0 g, 8.54 mmol) and 2-butenoyl chloride (2.4 mL, 25.0 mmol) was added styrene (30 mL), followed by CuCl (0.1 g). The reaction mixture was stirred at 114° C. for 16 h. It was then cooled to room temperature and evaporated to give a white residue, which was dissolved in DCM and washed with water, brine and dried over MgSO4. The solution was concentrated and the addition of pentane to the residue furnished the product as a white precipitate. Yield 76% (0.93 g). m.pt. 149–150° C. 1H NMR: δ 1.94 (dd, 1H, CH3CH, 2JHH=6.8 Hz, 3JHH=1.4 Hz); 3.78 (s, 3H, OCH3); 6.84 (dd, 1H, COCH, 2JHH=15.0 Hz, 3JHH=1.3 Hz); 7.10–7.20 (m, 1H, CH3CH); 7.89 (s, br, 1H, NH). 13C NMR: δ 18.4 (CH3CH), 53.0 (OCH3), 122.7 (COCH), 146.6 (CH3CH), 152.4 (CO2), 166.1 (COCH). m/z (HR-EIMS) Expected 143.0582 (M+), observed 143.0577. Anal. calcd for C9H9NO3: C, 50.35; H, 6.34; N, 9.79%. Found: C, 50.44; H, 6.59; N, 9.94%.

Workup

  1. temperatureIt was then cooled to room temperature
  2. customevaporated
  3. customto give a white residue, which
  4. washwashed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationThe solution was concentrated
  7. additionthe addition of pentane to the residue
  8. customfurnished the product as a white precipitate

Sources & evidence

ORD record
ord-d52e5b87cdf348c2ac2530d7a0cee208
Source dataset
uspto-grants-2007_06
Patent number
US07232923B2

Reaction notes

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