Triethylamine → HCID 178511150, compound

HRID 2283198Notes

Reaction equation

HRID 2283198 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]([CH2:12][C:13]#[N:14])=[N:3]1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26]>O1CCOCC1>[CH:9]1[CH:10]=[C:11]2[C:2]([NH:3]/[C:4](/[NH:5][C:6]2=[CH:7][CH:8]=1)=[C:12](/[C:25]([C:24]1[CH:28]=[CH:29][C:30]([Cl:32])=[CH:31][C:23]=1[Cl:22])=[O:26])\[C:13]#[N:14])=[O:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 178510890HCID 178510890, compound

Product 1

HCID 178511150HCID 178511150, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To solution of 2-(4-oxo-1.4-dihydroquinazolin-2-yl)acetonitrile (202 mg, 1.09 mmol) and triethylamine (167 μL, 1.20 mmol) in dioxane (8 mL) was added 2.4-dichlorobenzoyl chloride (152 μL, 1.09 mmol), 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 A (1) (213 mg, 53%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.46-7.50 (m, 1H), 7.52 (d. 1=8.2 Hz, 1H), 7.56 (dd, J1=8.2, J2=1.9 Hz, 1H), 7.77 (d, J=2.0 Hz, 1H), 7.83-7.88 (m, 2H), 8.07 (d, J=8.1 Hz, 1H). 13C NMR (500 MHz, DMSO-d6) δ ppm 71.74, 117.43, 117.54, 118.71, 125.92, 126.68, 127.66, 129.21, 129.66, 130.49, 134.85, 135.85, 138.15, 139.25, 155.01, 158.3, 188.75. HRMS (m/z): [M+ calc. for C17H9N3O2Cl2Na, 379.9970; observed, 379.9967.

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-1fd876a3e07e48548695cb0e55bc300f
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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