HuagongsheHuagongshe Chemistry Print Report · For research reference only
Citric Acid → 7-Nitro-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro- | HCID 20821 | — |
| Reactant | methyl N'-(chloromethylsulfonyl)carbamimidothioate | HCID 178504066 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Product | 7-Nitro-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide | HCID 135740306 | — |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04904667 |
| Source dataset | uspto-grants-1990_02 |
| ORD ID | ord-00feb850b34b41dfaaff225dc0488ed2 |
| Source note | uspto-grants-1990_02 |