N-methyl-2-pyrrolidone → 7,8-Dichloro-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

HRID 1199973Notes

Reaction equation

HRID 1199973 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=O)O[C:6](=[O:7])[C:5]2=[CH:12][C:13]=1[Cl:14].[H-].[Na+].CSC(=N)[NH:20][S:21]([CH2:24]Cl)(=[O:23])=[O:22].C[N:28]1CCCC1=O>>[Cl:14][C:13]1[CH:12]=[C:5]2[C:4](=[CH:3][C:2]=1[Cl:1])[N:10]=[C:9]1[NH:20][S:21](=[O:22])(=[O:23])[CH2:24][N:28]1[C:6]2=[O:7]

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 127247274,5-Dichloroisatoic anhydrideHCID 178504066methyl N'-(chloromethylsulfonyl)carbamimidothioate

Product 1

HCID 1357403097,8-Dichloro-1H-1,2,4-thiadiazolo[3,4-b]quinazolin-5-one-2,2-dioxide

Procedure

To a stirred slurry of 4,5-dichloroisatoic anhydride (11.54 g, 50 mmol) in N-methyl-2-pyrrolidinone (50 ml) under nitrogen is added sodium hydride (2.05 g of 60% oil dispersion, 52 mmol). The mixture is stirred for 30 min at room temperature, and to the resulting solution is added S-methyl-N-(chloromethanesulfonyl)-isothiourea (11.0 g, 55 mmol). The mixture is stirred under nitrogen at 80° C. for 18 hr, then worked up as in Example 4 above. Recrystallization from DMF provides the title compound as a white solid, mp >300° C. (4.69 g, 31%).

Workup

  1. stirringThe mixture is stirred under nitrogen at 80° C. for 18 hr
  2. customRecrystallization from DMF

Sources & evidence

ORD record
ord-08995a06154b4b48a071df0b6120604d
Source dataset
uspto-grants-1990_02
Patent number
US04904667

Reaction notes

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