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

HRID 52632Notes

Reaction equation

HRID 52632 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

5

Reactant 3

HCID 9237DabcoHCID 14923Ammonium HydroxideHCID 442641426-[(3,4-Dichlorophenyl)sulfanyl]quinazoline-2,4-diamine

Product 1

HCID 125559782,4-Diamino-6-(3,4-dichlorophenylsulfinyl)quinazoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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.

Workup

  1. additionUpon completion of addition
  2. stirringthe reaction mixture was stirred at ambient temperature for about 20 hours
  3. filtrationThe resultant solid was collected by filtration
  4. customtriturated with methanol
  5. filtrationThe solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ef29a30e667643a58f11b9fcbd0097d0
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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