2-Amino-5-methylbenzophenone → 2-(1-Methoxyethylideneamino)-5-methylbenzophenone
Reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:17]([O-])([O-])([O:19][CH3:20])[CH3:18]>>[CH3:20][O:19][C:17](=[N:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:18]Participants
Procedure
2-Amino-5-methylbenzophenone is reacted with methyl orthoacetate, whereby 2-(1-methoxyethylideneamino)-5-methylbenzophenone is obtained. The product is reacted with hydrazine hydrate, whereby 3-amino-3,4-dihydro-2, 6-dimethyl-4-hydroxy-4-phenylquinazoline (colorless peates melting at 192° to 196° C) is obtained. The product is reacted with chloroacetylchloride, followed by the same treatment as Example 1, whereby 3-chloroacetylamino-3, 4-dihydro-2, 6-dimethyl-4-hydroxy-4-phenylquinazoline having 1/2 mole of water of crystallization (colorless powdery crystals melting at 90° to 93° C) is obtained. The product is heated with acetic acid, whereby crystals of 2-(3-chloromethyl-1-methyl-s-triazol-4-yl)-5-methylbenzophenene are obtained. Recrystallization from benzene gives colorless needles melting at 167° to 168° C. Overall yield: 42%.
Sources & evidence
- ORD record
- ord-6928c770fa46479da73b8c55b498c014
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04082764
Reaction notes
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