Dimethyl Sulfoxide → Sulfametrole

HRID 26637Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:7](Cl)=[N:6][S:5][N:4]=1.[S:9]([NH2:19])(=[O:18])([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>>[CH3:1][O:2][C:3]1[C:7]([NH:19][S:9]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)(=[O:10])=[O:18])=[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 96.05%

Procedure

75.3 g of 3-methoxy-4-chloro-1,2,5-thiadiazole (0.5 mole), 103.32 g of sulfanilamide (0.6 mole) and 207.31 g of potassium carbonate (1.5 mole) were reacted in 195.33 g of dimethysulfoxide (2.5 mole) and worked up as described in Example 2. 137.5 g of crude 3-methoxy-4-(4'-aminobenzene-sulfonamido)-1,2,5-thiadiazole (96.05% of theory) were obtained. The mixture was recrystallized from methanol/water 1:1 with charcoal added, as described in Example 2. 126.87 g of pure product (88.63% of theory) having a melting point of 149°-150° C. were obtained; the product showed no additional spots in TLC and met the colour standard.

Sources & evidence

ORD record: ord-129559c4881f465595bc1067db89ef4b
Source dataset: uspto-grants-1979_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04151164

Reaction notes

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