Dabco → 2,4-Diamino-6-(3,4-dichlorophenylsulfinyl)quinazoline

Reaction equation

N12CCN(CC1)CC2.[NH2:9][C:10]1[N:19]=[C:18]([NH2:20])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([S:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH:16]=2)[N:11]=1.[OH-:30].[NH4+]>C(O)(=O)C>[NH2:9][C:10]1[N:19]=[C:18]([NH2:20])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([S:21]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)=[O:30])[CH:16]=2)[N:11]=1

Participants

Procedure

A suspension of 5.0 grams (0.011 mole) of the bromine complex of 1,4-diazabicyclo(2,2,2)octane in 200 mL of aqueous 70% acetic acid was stirred, and 3.4 grams (0.01 mole) of 2,4-diamino-6-(3,4-dichlorophenylthio)quinazoline was added portionwise during about a 1 hour period. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 20 hours. After this time, the reaction mixture was neutralized with concentrated ammonium hydroxide. The resultant solid was collected by filtration and triturated with methanol. The solid was collected by filtration and dried, yielding 2,4-diamino-6-(3,4-dichlorophenylsulfinyl)quinazoline, mp 200° C., dec. The NMR spectrum was consistent with the proposed structure.