Dimethyl Sulfoxide → Sulfametrole

HRID 26635Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:7](Cl)=[N:6][S:5][N:4]=1.CS(C)=O.[S:13]([NH2:23])(=[O:22])([C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3]1[C:7]([NH:23][S:13]([C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)(=[O:14])=[O:22])=[N:6][S:5][N:4]=1

Participants

Reactant 4

HCID 679Dimethyl Sulfoxide

HCID 5333Sulfanilamide

HCID 11430Potassium Carbonate

HCID 181772483-Chloro-4-methoxy-1,2,5-thiadiazole

Product 1

HCID 64939SulfametroleYield 96.82%

Procedure

150.6 g of 3-methoxy-4-chloro-1,2,5-thiadiazole (1 mole) were suspended in 390.65 g (5 mole) of dimethyl sulfoxide, and 258.31 g of sulfanilamide (1.5 mole) and 414.63 g of potassium carbonate (3 mole) were added. The mixture was left to react for 10 days at temperatures of 28°-30° C., and was then worked up according to Example 1. 277.2 g of crude 3-methoxy-4-(4'-aminobenzenesulfonamido)-1,2,5-thiadiazole were obtained, corresponding to a yield of 96.82% of theory. Melting point: 144°-147° C.

Workup

waitThe mixture was left
customto react for 10 days at temperatures of 28°-30° C.

Sources & evidence

ORD record: ord-f635db51e4154386a9985ab3756a6879
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151164

Reaction notes

Loading…