Ethyl Bromide → HCID 178510891, compound

HRID 2283203Notes

Reaction equation

HRID 2283203 reaction equation
[C:1]([CH2:3][C:4](=S)[NH2:5])#[N:2].BrCC.[O-]CC.[Na+].[NH2:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O>>[Cl:24][C:22]1[CH:23]=[C:15]2[C:16]([C:17](=[O:19])[N:5]=[C:4]([CH2:3][C:1]#[N:2])[NH:14]2)=[CH:20][CH:21]=1

Participants

5

Reactant 4

HCID 6332Ethyl BromideHCID 666462-Amino-4-chlorobenzoic acidHCID 14162772-CyanoethanethioamideHCID 2723922Sodium ethoxide

Product 1

HCID 178510891HCID 178510891, compoundYield 18.5%

Procedure

2-cyanoethanethioamide (300 mg, 3.00 mmol) and bromoethane (299 μL, 4.00 mmol) were added to an ethanolic solution of sodium ethoxide (4.00 mmol, 3 mL). The resulting mixture was stirred for 6 hours, 2-amino-4-chlorobenzoic acid (500 mg, 2.91 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-(7-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (118 mg, 18%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.19 (s, 2H), 7.57 (dd, J1=8.5 Hz, J2=2.1 Hz, 1H), 7.74 (d, J=2.0 Hz, 1H), 8.09 (d, J=8.4 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-e7dc31e733c5445da22f22db72893ed5
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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