Triethylamine → HCID 178511151, compound

HRID 2283204Notes

Reaction equation

HRID 2283204 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:15])[N:7]=[C:8]([CH2:12][C:13]#[N:14])[NH:9]2)=[CH:4][CH:3]=1.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:3]1[C:2]([Cl:1])=[CH:11][C:10]2[NH:9]/[C:8](/[NH:7][C:6](=[O:15])[C:5]=2[CH:4]=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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 178510891HCID 178510891, compound

Product 1

HCID 178511151HCID 178511151, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To solution of 2-(7-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (24.9 mg, 113 μmol) and triethylamine (17.4 μL, 125 μmol) in dioxane (4 mL) was added 2,4-dichlorobenzoyl chloride (15.9 μL, 113 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 D (5) (11.4 mg, 26%). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.47-7.52 (m, 2H), 7.56 (dd, J1=8.2 Hz, J2=1.8 Hz, 1H), 7.77 (d, J1=1.8 Hz, 1H), 7.90 (br s, 1H), 8.04 (d, J=8.5 Hz, 1H). 13C NMR (500 MHz, DMSO-d6) δ ppm 72.44, 116.56, 118.79, 118.85, 125.74, 127.65, 128.66, 129.2, 129.65, 130.49, 134.81, 138.21, 140.03, 155.62, 157.98, 188.6. HRMS (m/z): [M+Na]+ calc. for C17H8N3O2Cl3Na, 413.9580; observed, 413.9583.

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-9a96bd854980498691ff24b07f37c22c
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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