Citric Acid → 7-Nitro-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

HRID 1199970

Reaction equation

HRID 1199970 reaction equation
[N+:1]([C:4]1[CH:15]=[C:8]2[C:9]([O:11][C:12](=O)[NH:13][C:7]2=[CH:6][CH:5]=1)=O)([O-:3])=[O:2].CSC(=N)[NH:19][S:20]([CH2:23]Cl)(=[O:22])=[O:21].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(#[N:41])C>CN(C1C=CN=CC=1)C>[N+:1]([C:4]1[CH:15]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:13]=[C:12]1[NH:19][S:20](=[O:21])(=[O:22])[CH2:23][N:41]1[C:9]2=[O:11])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6342AcetonitrileHCID 208212H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-HCID 178504066methyl N'-(chloromethylsulfonyl)carbamimidothioate

Product 1

HCID 1357403067-Nitro-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a stirred solution of 5-nitroisatoic anhydride (1.04 g, 5.0 mmol) and S-methyl-N-(chloromethanesulfonyl)isothiourea (1.04 g, 5.0 mmol) in acetonitrile (10 ml) under nitrogen is added 4-(N,N-dimethylamino)-pyridine (0.61 g, 5.0 mmol). The solution is refluxed for 16 hr, cooled, and poured into 10% aqueous citric acid. The resulting solid is collected by filtration and recrystallized twice from isopropanol/DMF, then from DMSO, to provide the title compound as a light yellow solid, mp >300° C. (225 mg, 16%).

Workup

  1. temperatureThe solution is refluxed for 16 hr
  2. temperaturecooled
  3. filtrationThe resulting solid is collected by filtration
  4. customrecrystallized twice from isopropanol/DMF

Sources & evidence

ORD record
ord-00feb850b34b41dfaaff225dc0488ed2
Source dataset
uspto-grants-1990_02
Patent number
US04904667

Linked notes

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