Anthranilic Acid → 3,4-Dihydro-4-oxo-2-quinazolineacetonitrile

HRID 2283197Notes

Reaction equation

HRID 2283197 reaction equation
[C:1]([CH2:3][C:4](=S)[NH2:5])#[N:2].BrCC.[O-]CC.[Na+].[NH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O>>[O:19]=[C:17]1[C:16]2[C:15](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:14]=[C:4]([CH2:3][C:1]#[N:2])[NH:5]1

Participants

5

Reactant 4

HCID 227Anthranilic AcidHCID 6332Ethyl BromideHCID 14162772-CyanoethanethioamideHCID 2723922Sodium ethoxide

Product 1

HCID 1354090773,4-Dihydro-4-oxo-2-quinazolineacetonitrileYield 47.1%

Procedure

2-Cyanoethanethioamide (1.00 g, 10.0 mmol) and bromoethane (821 μL, 11.0 mmol) were added to an ethanolic solution of sodium ethoxide (11.5 mmol, 5.3 mL). The resulting mixture was stirred for 6 hours, 2-aminobenzoic acid (1.50 g, 10.9 mmol) was added, and the reaction 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 ethanol, water, ethanol, and diethyl ether. The solid was then dried to yield 2-(4-oxo-3,4-dihydroquinazolin-2-yl)acetonitrile (872 mg, 47%). 1NMR (400 MHz, DMSO-d6) δ ppm 4.17 (s, 2H), 7.53 (t, J=7.5 Hz, 1H), 7.68 (d, J=7.9 Hz, 1H), 7.83 (t, J=7.8 Hz, 1H), 8.10 (dd, J1=7.9 Hz, J2=1.2 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-87dd7746e3de4960a9932acef889498b
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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