Dimethyl Sulfoxide → Sulfametrole

HRID 26636Notes

Reaction equation

HRID 26636 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

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5333SulfanilamideHCID 11430Potassium CarbonateHCID 181772483-Chloro-4-methoxy-1,2,5-thiadiazole

Product 1

HCID 64939SulfametroleYield 86%

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 712.25 g of potassium carbonate (1.25 mole) were reacted in 78.13 g of dimethyl sulfoxide (1 mole) and were further treated as described in Example 1. 123.1 g of crude 3-methoxy-4-(4'-aminobenzene-sulfonamido)-1,2,5-thiadiazole (85.99% of theory) were obtained.

Workup

  1. additionwere further treated

Sources & evidence

ORD record
ord-bc8fb7d44eeb405193a328ad00329943
Source dataset
uspto-grants-1979_04
Patent number
US04151164

Reaction notes

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