Hydrochloric Acid → Sulfametrole

HRID 26634Notes

Reaction equation

HRID 26634 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+].Cl>O>[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 5333SulfanilamideHCID 11430Potassium CarbonateHCID 181772483-Chloro-4-methoxy-1,2,5-thiadiazole

Product 1

HCID 64939SulfametroleYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150.6 g of 3-methoxy-4-chloro-1,2,5-thiadiazole (1 mole) were suspended in 156.26 g of dimethyl sulfoxide (2 mole) and 258.31 g of sulfanilamide (1.5 mole) and 414.63 g of potassium carbonate (3 mole) were then added. The mixture was kept at 70° C. for 48 hours while stirring. 600 ml of water were then added, the mixture was cooled to ambient temperature and adjusted to pH 1.5 with concentrated hydrochloric acid. The precipitated crystallized material was filtered off, washed with water and dried. A yield of 271.1 g of crude 3-methoxy-4-(4'-aminobenzenesulfonamido)-1,2,5-thiadiazole (94.67% of theory), melting point 138°-146° C., was obtained.

Workup

  1. customThe precipitated crystallized material
  2. filtrationwas filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-465fd41c1f3c446db97935adfb6ccdaa
Source dataset
uspto-grants-1979_04
Patent number
US04151164

Reaction notes

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