Ethyl Bromide → HCID 178510892, compound

HRID 2283201Notes

Reaction equation

HRID 2283201 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][C:21]([Cl:24])=[CH:20][C:16]=1[C:17]([OH:19])=O>>[Cl:24][C:21]1[CH:20]=[C:16]2[C:15](=[CH:23][CH:22]=1)[NH:14][C:4]([CH2:3][C:1]#[N:2])=[N:5][C:17]2=[O:19]

Participants

5

Reactant 4

HCID 6332Ethyl BromideHCID 124762-Amino-5-chlorobenzoic acidHCID 14162772-CyanoethanethioamideHCID 2723922Sodium ethoxide

Product 1

HCID 178510892HCID 178510892, compoundYield 29%

Procedure

2-cyanoethanethioamide (501 mg, 5.00 mmol) and bromoethane (448 μL, 6.00 mmol) were added an ethanolic solution of sodium ethoxide (6.00 mmol, 3 mL). The resulting mixture was stirred for 6 hours, 2-amino-5-chlorobenzoic acid (858 mg, 5.00 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-(6-chloro-4-oxo-1,4-dihydroquinazolin-2-yl)acetonitrile (314 mg, 29%). 1H NMR (500 MHz, DMSO-d6) δ ppm 4.18 (s, 2H), 7.70 (d, J=8.8 Hz, 1H), 7.85 (dd, J1=8.7 Hz, J2=2.0 Hz, 1H) 8.03 (d, J=2.4 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-33bb339e79894ec2b125faca6f4cd9e9
Source dataset
uspto-grants-2015_09
Patent number
US09145376B2

Reaction notes

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