N,N-dimethyl-p-phenylenediamine → (4-Dimethylamino-phenyl)-(2-methyl-quinazolin-4-yl)-amine

HRID 1668788Notes

Reaction equation

HRID 1668788 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[N:3]=1.[CH3:13][N:14]([CH3:22])[C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.C([O-])(=O)C.[Na+]>>[CH3:13][N:14]([CH3:22])[C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[N:3]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 517045Sodium AcetateHCID 27854214-Chloro-2-methylquinazoline

Product 1

HCID 59648373(4-Dimethylamino-phenyl)-(2-methyl-quinazolin-4-yl)-amine

Procedure

The title compound was prepared from 4-chloro-2-methyl-quinazoline (178.6 mg, 1.0 mmol), 4-dimethylamino-aniline (136.2 mg, 1.0 mmol) and sodium acetate (98.4 mg, 1.2 mmol) similar to example 20 to give 222 mg (79.9%) of gray solids. 1H NMR (CDCl3): 7.82-7.70 (m, 3H), 7.62 (d, J=9.0 Hz, 2H), 7.45 (t, J=7.5 Hz, 1H), 6.80 (d, J=9.0 Hz, 2H), 2.97 (s, 6H), 2.66 (s, 3H).

Sources & evidence

ORD record
ord-9d9e056fd6584b0c895e998e6aeca2d5
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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