2,6-Dichloroaniline → HCID 178522610, compound

HRID 275034Notes

Reaction equation

HRID 275034 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[C:10]([NH:18][C:19]1[NH:23][N:22]=[C:21]([S:24](Cl)(=[O:26])=[O:25])[N:20]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:10]([NH:18][C:19]1[NH:23][N:22]=[C:21]([S:24]([NH:4][C:3]2[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=2[Cl:9])(=[O:26])=[O:25])[N:20]=1)(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 118462,6-DichloroanilineHCID 178522609HCID 178522609, compound

Product 1

HCID 178522610HCID 178522610, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A small flask equipped with a magnetic stirrer and protected from the atmosphere by a drying tube was charged with 8.1 g (0.05 mole) of 2,6-dichloroaniline, 20 ml of dry pyridine and then 14.4 g (0.05 mole) of dry 5-benzoylamino-3-chlorosulfonyl-1,2,4-triazole was added over about 1 minute with vigorous stirring. After the exotherm had subsided somewhat, the mixture was heated with an oil bath maintained at 100°-106° C. for 3 hours with stirring. The mixture was next concentrated under reduced pressure on a rotary evaporator to remove the bulk of the pyridine (80° C./1 mm) and then taken up in a mixture of 25 ml of concentrated aqueous ammonia, 125 ml of water and 100 ml of methylene chloride. After cooling and filtration to remove the insoluble material, the methylene chloride phase was removed and the pH of the aqueous phase was adjusted to 2.5 with hydrochloric acid. The precipitate that formed was collected by filtration, washed with watery and dried to obtain 10.2 g (50 percent of theory) of the title sulfonamide. A sample purified by recrystallization from acetonitrile melted at 321°-322° (dec.). The carbon nmr spectrum was consistent with the assigned structure, having absorptions at 159.2, 149.7, 165.6, 135.9, 130.8, 128.9, 130.0, 132.8, 128.6, 128.1, and 131.7 ppm.

Workup

  1. customA small flask equipped with a magnetic stirrer
  2. customprotected from the atmosphere by a drying tube
  3. temperaturethe mixture was heated with an oil bath
  4. temperaturemaintained at 100°-106° C. for 3 hours
  5. concentrationThe mixture was next concentrated under reduced pressure on a rotary evaporator
  6. customto remove the bulk of the pyridine (80° C./1 mm)
  7. additiontaken up in a mixture of 25 ml of concentrated aqueous ammonia, 125 ml of water and 100 ml of methylene chloride
  8. temperatureAfter cooling
  9. filtrationfiltration
  10. customto remove the insoluble material
  11. customthe methylene chloride phase was removed
  12. customThe precipitate that formed
  13. filtrationwas collected by filtration
  14. washwashed with watery
  15. customdried

Sources & evidence

ORD record
ord-a57292626b6043da969418b5a659bfd7
Source dataset
uspto-grants-1995_02
Patent number
US05391759

Reaction notes

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