Aniline → 2-Chloro-4-phenyl-amino-quinazoline

HRID 50530Notes

Reaction equation

HRID 50530 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([N:16](CC)C(C)C)(C)C.N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[Cl:1][C:2]1[N:11]=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH2:16])[N:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2528862,4-Dichloroquinazoline

Product 1

HCID 226398082-Chloro-4-phenyl-amino-quinazoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2,4-dichloro-quinazoline (15 g), N,N-diisopropyl-ethylamine (24.9 ml) and aniline (7.5 ml) in isopropanol (75 ml) is heated to reflux for 45 min. The cold reaction mixture is filtered and the filtrate is concentrated in vacuo. The residue is crystallized from diethylether-toluene (1:1) to give 2-chloro-4-phenyl-amino-quinazoline, m.p. 194-196° C.

Workup

  1. temperatureto reflux for 45 min
  2. customThe cold reaction mixture
  3. filtrationis filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe residue is crystallized from diethylether-toluene (1:1)

Sources & evidence

ORD record
ord-863117d32ae64f76915b8f912d2e142a
Source dataset
uspto-grants-2004_03
Patent number
US06713265B1

Reaction notes

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