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

HRID 614904Notes

Reaction equation

HRID 614904 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 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of cyanogen bromide (89.6 g, 0.85 mol) in toluene (1.6 liters) was poured into a solution of N-(6-amino-2,3-dichlorobenzyl)glycine ethyl ester (231 g, 0.834 mol) in toluene (1.6 liters). The temperature rose quickly from 18° to 31°. The mixture was slowly (1 hour) heated to reflux and refluxed for 12 hours. The mixture was cooled to room temperature and filtered, the product being washed with toluene both by decantation and on the filter. The residue was washed with ether and then dried under pump vacuum (0.5-1 mm Hg) over P2O5. A yield of 290 g (91%) of the title product was obtained as a brown powder. When heated this powder decomposed over a wide temperature range: 200°-300°.

Workup

  1. customrose quickly from 18° to 31°
  2. custom(1 hour)
  3. temperatureheated
  4. temperatureto reflux
  5. temperaturerefluxed for 12 hours
  6. filtrationfiltered
  7. washthe product being washed with toluene both by decantation
  8. washThe residue was washed with ether
  9. dry with materialdried under pump vacuum (0.5-1 mm Hg) over P2O5

Sources & evidence

ORD record
ord-d2ff283c5c1c43e78ce0f5db3de6640d
Source dataset
uspto-grants-1979_03
Patent number
US04146718

Reaction notes

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