Mucochloric Acid → HCID 13772910, compound

HRID 1906301Notes

Reaction equation

HRID 1906301 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])(=[O:10])=[O:9])[N:3]=1.[C:18](O)(=O)/[C:19](=[C:21](\C=O)/Cl)/[Cl:20]>CN(C=O)C>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[S:8]([NH:7][C:4]1[N:3]=[C:2]2[N:1]=[CH:18][C:19]([Cl:20])=[CH:21][N:6]2[N:5]=1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 2771871Mucochloric AcidHCID 13772885HCID 13772885, compound

Product 1

HCID 13772910HCID 13772910, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.46 g (9.00 mmol) of N-(5-amino-1,2,4-triazol-3-yl)-2-chlorobenzenesulfonamide and 1.67 g (9.90 mmol) of mucochloric acid in 20 ml of DMF was heated to reflux for 16.5 hours. After cooling to room temperature, the solvent was removed by evaporation at reduced pressure and the residue was treated with 20 ml of 0.5N NaOH. After stirring vigorously for ~30 minutes the mixture was filtered through celite and the filtrate was acidified with 2N HCl. The solid which separated was collected by filtration, washed with water and recrystallized from acetic acid--water to yield 0.70 g (23 percent) of the desired product as a light brown solid, mp 256.5°-260.5° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16.5 hours
  3. customthe solvent was removed by evaporation at reduced pressure
  4. additionthe residue was treated with 20 ml of 0.5N NaOH
  5. filtrationwas filtered through celite
  6. customThe solid which separated
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-fd77b559f6c24215bfa2c354a472a8d7
Source dataset
uspto-grants-1987_03
Patent number
US04650892

Reaction notes

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