Cyanogen Bromide → ethyl 2-(2-amino-5,6-dichloro-4H-quinazolin-3-yl)acetate;hydrobromide

HRID 614903Notes

Reaction equation

HRID 614903 reaction equation
[N:1]#[C:2][Br:3].[CH2:4]([O:6][C:7](=[O:20])[CH2:8][NH:9][CH2:10][C:11]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]([Cl:18])[C:12]=1[Cl:19])[CH3:5]>C1(C)C=CC=CC=1>[CH3:5][CH2:4][O:6][C:7]([CH2:8][N:9]1[C:2]([NH2:1])=[N:17][C:16]2[CH:15]=[CH:14][C:13]([Cl:18])=[C:12]([Cl:19])[C:11]=2[CH2:10]1)=[O:20].[BrH:3]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 9814186Ethyl 2-((6-amino-2,3-dichlorobenzyl)amino)acetate

Product 1

HCID 9999996ethyl 2-(2-amino-5,6-dichloro-4H-quinazolin-3-yl)acetate;hydrobromideYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of cyanogen bromide (0.53 gm. 5 mmol) in toluene (10 ml.) was added to a solution of N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester (1.39 gm, 5 mmol) in toluene (10 ml.) and stirred at room temperature. There was an almost immediate precipitate. Stirring was continued for 30 minutes, and the reaction mixture was then heated to reflux and refluxed for 18 hours. After cooling, the solid was filtered off, washed with toluene and dried to give 1.81 gm (94.5%) of the title product. A portion of the product was recrystallized from ethanol, washed with ethanol and ether, and dried in vacuo at 78° to give an analytical sample as golden crystals.

Workup

  1. stirringStirring
  2. temperaturethe reaction mixture was then heated
  3. temperatureto reflux
  4. temperaturerefluxed for 18 hours
  5. temperatureAfter cooling
  6. filtrationthe solid was filtered off
  7. washwashed with toluene
  8. customdried

Sources & evidence

ORD record
ord-e94c0f308e624959be93a06cfd570ecb
Source dataset
uspto-grants-1979_03
Patent number
US04146718

Reaction notes

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