Dimethyl Sulfide → N-(2,6-dichlorophenyl)-7,8-dichloro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide

HRID 1953202Notes

Reaction equation

HRID 1953202 reaction equation
CSC.ClCl.[Cl:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:8]=1[NH2:9].N1C2C(=CC=CC=2)C=CC=1.Cl[S:26]([C:29]1[N:37]=[C:36]2[N:31]([CH:32]=[N:33][C:34]([Cl:39])=[C:35]2[Cl:38])[N:30]=1)(=[O:28])=[O:27]>ClCCl.[SH2]=N.CO>[Cl:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:8]=1[NH:9][S:26]([C:29]1[N:37]=[C:36]2[N:31]([CH:32]=[N:33][C:34]([Cl:39])=[C:35]2[Cl:38])[N:30]=1)(=[O:28])=[O:27]

Participants

9

Reactant 5

HCID 1068Dimethyl SulfideHCID 7047Quinoline2×HCID 118462,6-Dichloroaniline2×HCID 24526ChlorineHCID 233039162-Chlorosulfonyl-7,8-dichloro[1,2,4]triazolo[1,5-c]pyrimidine

Product 1

HCID 23303914N-(2,6-dichlorophenyl)-7,8-dichloro[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 178514670HCID 178514670, compoundCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.6 mL (8 mmol) of dimethyl sulfide in 65 mL of dichloromethane was cooled to -20° C. and then 0.4 g (6 mmol) of chlorine was slowly sparged in with stirring and cooling to maintain the temperature below -15° C. A mixture of 5.0 g (31 mmol) of 2,6-dichloroaniline and 6.3 g (49 mmol) of quinoline was then added with cooling and stirring to form a mixture of the sulfilimine catalyst, unreacted 2,6-dichloroaniline, and quinoline. The mixture was allowed to warm to 0° C. and 10 g (45 mmol) of 2-chlorosulfonyl-7,8-dichloro[1,2,4]triazolo[1,5-c]pyrimidine was added with stirring and cooling. The mixture was allowed to warm to about 20° C. and stir for about 16 hours. It was then diluted with 50 mL of methanol and the solids that formed were collected by filtration, washed 2×30 mL with methanol, and dried to obtain 6.2 g (80 percent of theory) of the title compound as a white solid having uv maxima at 210 and 270 nm.

Workup

  1. temperaturecooling
  2. temperatureto maintain the temperature below -15° C
  3. additionwas then added
  4. temperaturewith cooling
  5. stirringstirring
  6. customto form
  7. stirringwith stirring
  8. temperaturecooling
  9. temperatureto warm to about 20° C.
  10. stirringstir for about 16 hours
  11. customthe solids that formed
  12. filtrationwere collected by filtration
  13. washwashed 2×30 mL with methanol
  14. customdried

Sources & evidence

ORD record
ord-e41bc27f520f48b695fba75bcd47bd61
Source dataset
uspto-grants-2000_09
Patent number
US06114580

Reaction notes

Loading…