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ChemicalBook CAS DataBase List 6-BROMO-2-QUINAZOLINAMINE
190273-89-3

6-BROMO-2-QUINAZOLINAMINE synthesis

6synthesis methods
-

Yield:190273-89-3 73%

Reaction Conditions:

in N,N-dimethyl acetamide at 150; for 5 h;

Steps:

6-Bromoquinazolin-2-amine (3).32

Guanidine carbonate (2) (4.47 g, 36.9 mmol) was added to a solution of 5-bromo-2-fluorobenzaldehyde (1) (5.00 g, 24.6 mmol) in dimethylacetamide (50 ml). The reaction mixture was heated at 150°C for 5 h. The progress of the reaction was monitored by TLC using AcOEt-hexane, 1:1, as eluent. The reaction mixture was cooled and quenched with ice water, and stirred for 30 min. Then the obtained solid was filtered off, and water was removed by azeotropic distillation with PhMe to get 4.00 g (73%) of compound 3. Mp 270-272°C. 1H NMR spectrum (300 MHz), δ, ppm (J, Hz): 7.04 (2H, s,NH2); 7.37 (1H, d, J = 9.0, H Ar); 7.78 (1H, dd, J = 9.0,J = 2.4, H Ar); 8.05 (1H, d, J = 2.4, H Ar); 9.09 (1H, s,H Ar). Mass spectrum, m/z: 225 [M+H]+.

References:

Babu, D. Suresh;Srinivasulu, Doddaga;Kotakadi, Venkata S. [Chemistry of Heterocyclic Compounds,2015,vol. 51,# 1,p. 60 - 66][Khim. Geterotsikl. Soedin.,2015,vol. 51,# 1,p. 60 - 66,7]

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