Ethyl chloroformate → (4-Bromo-2,6-dimethyl-phenyl)-carbamic acid ethyl ester

HRID 1820140Notes

Reaction equation

HRID 1820140 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:15]([O:14][C:12](=[O:13])[NH:6][C:5]1[C:7]([CH3:9])=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])[CH3:16]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 905494-Bromo-2,6-xylidine

Product 1

HCID 11644748(4-Bromo-2,6-dimethyl-phenyl)-carbamic acid ethyl esterYield 88.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

4-Bromo-2,6-dimethyl-aniline (10 g), ethyl chloroformate (5.4 g) and potassium carbonate (10.4 g) were mixed in tetrahydrofuran (100 mL) and heated to reflux for 16 hours, cooled, filtered and concentrated in vacuo. Heptane (200 mL) was added to the crude product, which was stirred for 30 minutes at 70° C. The mixture was filtered and concentrated in vacuo to furnish 12 g (88% yield) of the title compound as a solid. LC-MS (m/z) 273 (MH+); tR=2.95, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, CDCl3): 1.31 (t, 3H), 2.24 (s, 6H), 4.19 (q, 2H), 5.92 (b, 1H), 7.22 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionHeptane (200 mL) was added to the crude product, which
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5c07130aefb44e196b2687d60c1df26
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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