3-(Trifluoromethyl)aniline → 4-Chloro-8-methylquinazoline

HRID 1358729Notes

Reaction equation

HRID 1358729 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](C)[CH:10]=2)[NH:5][C:4](=O)[N:3]=1.F[C:15](F)(F)C1C=C(C=CC=1)N>C(O)C>[CH3:15][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][N:3]=[C:2]2[Cl:1]

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 178423498HCID 178423498, compound

Product 1

HCID 181856184-Chloro-8-methylquinazoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.45 g of 4-chloro 6-methyl quinazolone and 0.405 g, of m-trifluoromethylaniline in 20 ml ethanol were refluxed 1 hour. Treatment with aqueous Na2CO3 and extraction with CH2Cl2 gave 0.2 g of P15 as a white solid, mp-215° C., as the free base. NMR CDCl3 δ 8.78 (1H, S), 8.06 (2H, m), 7.86 (1H, d, J=7.6 Hz), 7.65 (2H, m), 7.54 (1H, t, J=8.0 Hz), 7.42 (1H, m), 2.58 (3H, S).

Workup

  1. extractionTreatment with aqueous Na2CO3 and extraction with CH2Cl2
  2. customgave 0.2 g of P15 as a white solid, mp-215° C.

Sources & evidence

ORD record
ord-a411e2e75638425d93539ad4c27676fc
Source dataset
uspto-grants-2003_07
Patent number
US06596878B2

Reaction notes

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