Triethylamine → HCID 178511152, compound

HRID 2283202Notes

Reaction equation

HRID 2283202 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH2:12][C:13]#[N:14])=[N:6][C:5]2=[O:15].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:30]1[C:31]([Cl:33])=[CH:32][C:24]([Cl:23])=[C:25]([C:26](/[C:12](/[C:13]#[N:14])=[C:7]2/[NH:8][C:9]3[CH:10]=[CH:11][C:2]([Cl:1])=[CH:3][C:4]=3[C:5]([NH:6]/2)=[O:15])=[O:27])[CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 178510892HCID 178510892, compound

Product 1

HCID 178511152HCID 178511152, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To solution of 2-(6-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (52.0 mg, 237 μmol) and triethylamine (36.3 μL, 260 μmol) in dioxane (4 mL) was added 2,4-dichlorobenzoyl chloride (33.1 μL, 237 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 C (4) (6.4 mg, 7%). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.50 (d, J1=8.3 Hz, 1H), 7.56 (dd, J1=8.3 Hz, J2=1.9 Hz, 1H), 7.77 (d, J=1.9 Hz, 1H), 7.83 (d, J=8.8 Hz, 1H), 7.88 (dd, J1=8.9 Hz, J2=2.3 Hz, 1H), 8.00 (d, J2=2.4 Hz, 1H). 13C NMR (500 MHz, DMSO-d6) δ ppm 72.1, 117.52, 118.98, 121.22, 125.61, 127.67, 129.22, 129.66, 129.99, 130.49, 134.88, 135.64, 38.11, 138.58, 155.05, 157.52, 188.76. 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-837f75eb02ec4aeca55e36c00a118b80
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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