Water → HCID 68711469, compound

HRID 1820113Notes

Reaction equation

HRID 1820113 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16](Cl)=[O:17].O>C(#N)C>[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16](=[O:17])[NH:6][C:5]1[C:7]([CH3:9])=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 694002-Methoxyethyl chloroformateHCID 905494-Bromo-2,6-xylidine

Product 1

HCID 68711469HCID 68711469, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

4-Bromo-2,6-dimethyl-aniline (2.00 g) and chloroformic acid 2-methoxyethyl ester (1.52 g) were dissolved in acetonitrile (25 mL) and heated to 130° C. for 15 minutes in a sealed microwave process vial. Water (25 mL) was added to the reaction mixture, and the product was collected by filtration and washed with water (25 mL) and heptane (25 mL) to furnish 2.48 g (82% yield) of the title compound as a white solid. LC-MS (m/z) 304 (MH+); tR=2.93, (UV, ELSD) 96%, 97%. 1H NMR (500 MHz, CDCl3): 2.36 (m, 6H), 3.40 (m, 3H), 3.60 (m, 2H), 4.35 (m, 2H), 6.55 (broad s, 1H), 7.45 (s, 2H).

Workup

  1. filtrationthe product was collected by filtration
  2. washwashed with water (25 mL) and heptane (25 mL)

Sources & evidence

ORD record
ord-bfca13f2f7f046daa6ed14f8b5922aef
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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