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

반응식

[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]

참가 물질

반응물 4

HCID 13387N-methyl-2-pyrrolidone

HCID 24758Sodium hydride

HCID 127247274,5-Dichloroisatoic anhydride

HCID 178504066methyl N'-(chloromethylsulfonyl)carbamimidothioate

생성물 1

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

실험 절차

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%).