Hydrochloric Acid → 6,7-Dimethoxy-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

HRID 1199972Notes

Reaction equation

HRID 1199972 reaction equation
[CH3:1][O:2][C:3]1[C:14]([O:15][CH3:16])=[C:7]2[C:8](O[C:11](=O)[NH:12][C:6]2=[CH:5][CH:4]=1)=[O:9].CSC(=N)[NH:20][S:21]([CH2:24]Cl)(=[O:23])=[O:22].[H-].[Na+].Cl.C[N:31]1CCCC1=O>>[CH3:16][O:15][C:14]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]2[C:7]=1[C:8](=[O:9])[N:31]1[CH2:24][S:21](=[O:22])(=[O:23])[NH:20][C:11]1=[N:12]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 127623805,6-Dimethoxyisatoic anhydrideHCID 178504066methyl N'-(chloromethylsulfonyl)carbamimidothioate

Product 1

HCID 1357403086,7-Dimethoxy-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 5,6-dimethoxyisatoic anhydride (8.93 g, 40 mmol) and S-methyl-N-(chloromethanesulfonyl)isothiourea (90% pure, 9.73 g, 44 mmol) in N-methyl-2-pyrrolidinone (50 ml) under nitrogen is added sodium hydride (1.65 g of 60% dispersion in oil, 41 mmol). After 15 min at room temperature, the mixture is stirred at 80° C. for 18 hr, then cooled and poured into 0.5N aqueous hydrochloric acid (150 ml). The precipitate is collected by filtration, and washed with water, then with ether. Recrystallization from DMF containing 5% water provides the title compound as a tan solid, mp >300° C. (2.55 g, 21%).

Workup

  1. temperaturecooled
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water
  4. customRecrystallization from DMF containing 5% water

Sources & evidence

ORD record
ord-bfa13fdf82ba4d0685ed73d67262efdb
Source dataset
uspto-grants-1990_02
Patent number
US04904667

Reaction notes

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