Heptanoyl chloride → HCID 11688185, compound

HRID 1820136Notes

Reaction equation

HRID 1820136 reaction equation
[C:1](Cl)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Br:10][C:11]1[CH:17]=[C:16]([CH3:18])[C:14]([NH2:15])=[C:13]([CH3:19])[CH:12]=1>C(#N)C>[Br:10][C:11]1[CH:17]=[C:16]([CH3:18])[C:14]([NH:15][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[C:13]([CH3:19])[CH:12]=1

Participants

4

Reactant 2

HCID 17313Heptanoyl chlorideHCID 905494-Bromo-2,6-xylidine

Product 1

HCID 11688185HCID 11688185, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Heptanoyl chloride (16 mg) was added to 4-bromo-2,6-dimethyl-aniline (20 mg) dissolved in acetonitrile and heated to 70° C. for 16 hours. The reaction mixture was concentrated in vacuo, redissolved in dimethyl sulfoxide/methanol (1:1, 0.5 mL) and subjected to preparative LC-MS purification to furnish 10 mg (33% yield) of the title compound as an oil. LC-MS (m/z) 313 (MH+); tR=3.33, (UV, ELSD) 93%, 100%.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in dimethyl sulfoxide/methanol (1:1, 0.5 mL)
  3. customsubjected to preparative LC-MS purification

Sources & evidence

ORD record
ord-ddc3d0ad6c3443e2a2c1a6f9fb0f2b47
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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