Hydrochloric Acid → 7,8-Dimethoxy-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

HRID 1199971Notes

Reaction equation

HRID 1199971 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[NH:11][C:10](=O)O[C:7](=[O:8])[C:6]2=[CH:13][C:14]=1[O:15][CH3:16].CSC(=N)[NH:20][S:21]([CH2:24]Cl)(=[O:23])=[O:22].[N:27]12CCCC1=NCCC2.Cl>O1CCOCC1>[CH3:16][O:15][C:14]1[CH:13]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[N:11]=[C:10]1[NH:20][S:21](=[O:22])(=[O:23])[CH2:24][N:27]1[C:7]2=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 27584236,7-Dimethoxy-2H-3,1-benzoxazine-2,4(1H)-dioneHCID 178504066methyl N'-(chloromethylsulfonyl)carbamimidothioate

Product 1

HCID 1357403077,8-Dimethoxy-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred slurry of 4,5-dimethoxyisatoic anhydride (4.46 g, 20 mmol) and S-methyl-N-(chloromethanesulfonyl)isothiourea (4.06 g, 20 mmol) in dioxane (30 ml) is added 1,5-diazabicyclo[4.3.0]non-5-ene (2.5 ml). The mixture is refluxed for 4 hr under nitrogen, then cooled and poured into 0.3N aqueous hydrochloric acid. The precipitate is collected by filtration and recrystallized from DMSO to provide the title compound as a light yellow solid, mp >300° C. (445 mg, 7.5%).

Workup

  1. temperatureThe mixture is refluxed for 4 hr under nitrogen
  2. temperaturecooled
  3. filtrationThe precipitate is collected by filtration
  4. customrecrystallized from DMSO

Sources & evidence

ORD record
ord-30dbeb41829a448a82c826ac282936ef
Source dataset
uspto-grants-1990_02
Patent number
US04904667

Reaction notes

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