Triethylamine → HCID 178511153, compound

HRID 2283200Notes

Reaction equation

HRID 2283200 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:15])[N:5]=[C:6]([CH2:12][C:13]#[N:14])[NH:7]2.C(N(CC)CC)C.[Cl:23][C:24]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>O1CCOCC1>[CH:10]1[CH:11]=[C:2]([Cl:1])[C:3]2[C:4]([NH:5]/[C:6](/[NH:7][C:8]=2[CH:9]=1)=[C:12](\[C:26]([C:25]1[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:24]=1[Cl:23])=[O:27])/[C:13]#[N:14])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 178510893HCID 178510893, compound

Product 1

HCID 178511153HCID 178511153, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To solution of 2-(5-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (26.4 mg, 120 μmol) and triethylamine (18.4 μL, 132 μmol) in dioxane (4 mL) was added 2,4-dichlorobenzoyl chloride (18.5 μL, 132 μmol), and the resulting mixture was refluxed overnight with stirring. A solid precipitate formed upon cooling of the reaction mixture, which was recovered by vacuum filtration and washed sequentially with methanol, water, methanol, and dichloromethane. The solid was then dried to yield ciliobrevin B (3) (12.8 mg, 27%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.46 (dd, J1=7.5 Hz, J2=1.4 Hz, 1H), 7.50 (d, J=8.2 Hz, 1H), 7.55 (dd. J1=8.2 Hz, J2=1.9 Hz, 1H), 7.68-7.79 (m, 3H). 13C NMR (500 MHz, DMSO-d6) δ ppm 71.69, 114.6, 117.63, 118.45, 127.65, 128.1, 129.2, 129.65, 130.49, 133.35, 134.8, 135.47, 138.2, 154.81, 156.48, 188.71. HRMS (m/z): [M+Na]+ calc. for C17H8N3O2Cl3Na, 413.9580; observed, 413.9582.

Workup

  1. temperaturethe resulting mixture was refluxed overnight
  2. customA solid precipitate formed
  3. temperatureupon cooling of the reaction mixture, which
  4. filtrationwas recovered by vacuum filtration
  5. washwashed sequentially with methanol, water, methanol, and dichloromethane
  6. customThe solid was then dried

Sources & evidence

ORD record
ord-6e8d01ceeafb408eb804c4eb9bc2e53b
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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