Hexanoyl chloride → HCID 3601868, compound

HRID 1820134Notes

Reaction equation

HRID 1820134 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[C:11](Cl)(=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C(#N)C>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH:6][C:11](=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:4]([CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 67340Hexanoyl chlorideHCID 905494-Bromo-2,6-xylidine

Product 1

HCID 3601868HCID 3601868, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

4-Bromo-2,6-dimethyl-aniline (0.50 g) and hexanoyl chloride (0.45 mL) were dissolved in acetonitrile (4 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction mixture was concentrated in vacuo and purified by flash chromatography to furnish 0.37 g (50% yield) of the title compound as a white solid. LC-MS (m/z) 299 (MH+); tR=3.09, (UV, ELSD) 100%, 99%. 1H NMR (500 MHz, CDCl3): 0.93 (t, 3H), 1.39 (m, 4H), 1.76 (qui, 2H), 2.20 (s, 6H), 2.40 (t, 2H), 6.57 (b, 1H), 7.23 (s, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a442f313bcc24a4f8d536d78c98b142d
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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