Ammonium Hydroxide → 4-(4-Benzoyl-3-chloroanilino)-6-(1-imidazolyl)-quinazoline

HRID 618681Notes

Reaction equation

HRID 618681 reaction equation
C(=O)(O)[O-].[Na+].[OH-].[NH4+].Cl[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N:19]3[CH:23]=[CH:22][N:21]=[CH:20]3)[CH:17]=2)[N:12]=[CH:11][N:10]=1.[NH2:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[C:27]([Cl:39])[CH:26]=1>>[C:29]([C:28]1[CH:37]=[CH:38][C:25]([NH:24][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N:19]4[CH:23]=[CH:22][N:21]=[CH:20]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:26][C:27]=1[Cl:39])(=[O:30])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 4

HCID 14923Ammonium HydroxideHCID 516892Sodium BicarbonateHCID 117364064-Amino-2-chlorobenzophenoneHCID 218478354-Chloro-6-(1-imidazolyl)quinazoline

Product 1

HCID 218478234-(4-Benzoyl-3-chloroanilino)-6-(1-imidazolyl)-quinazolineYield 11%

Procedure

Using an analogous procedure to that described in Example 4 except that the reaction product was basified by treatment with a saturated aqueous sodium bicarbonate solution rather than with a concentrated aqueous ammonium hydroxide solution, 4-chloro-6-(1-imidazolyl)quinazoline was reacted with 4-amino-2-chlorobenzophenone to give 4-(4-benzoyl-3-chloroanilino)-6-(1-imidazolyl)-quinazoline in 11% yield, m.p. 220-223° C.; NMR Spectrum: (CD3SOCD3) 7.2 (s, 1H), 7.5-7.8 (m, 6H), 7.9 (s, 1H), 8.0 (d, 1H), (m, 1H), 8.25 (m, 1H), 8.3 (d, 1H), 8.4 (s, 1H), 8.78 (s, 1H), 8.8 (d, 1H), 10.0 (broad s, 1H);

Sources & evidence

ORD record
ord-c943c84638914cf7ae72a30a7280de0b
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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