Hydrochloric Acid → N-(2,6-dichloro-3-methylphenyl)-7-ethoxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 1031377Notes

Reaction equation

HRID 1031377 reaction equation
[Na].[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:4]=1[NH:11][S:12]([C:15]1[N:25]=[C:18]2[N:19]=[C:20]([CH3:24])[CH:21]=[C:22](Cl)[N:17]2[N:16]=1)(=[O:14])=[O:13].Cl.[CH2:27]([OH:29])[CH3:28]>>[Cl:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([Cl:10])[C:4]=1[NH:11][S:12]([C:15]1[N:25]=[C:18]2[N:19]=[C:20]([CH3:24])[CH:21]=[C:22]([O:29][CH2:27][CH3:28])[N:17]2[N:16]=1)(=[O:13])=[O:14]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 5360545SodiumHCID 15017542N-(2,6-dichloro-3-methylphenyl)-7-chloro-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

Product 1

HCID 15017545N-(2,6-dichloro-3-methylphenyl)-7-ethoxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

Procedure

Sodium (0.69 g, 30 mmol) was added to about 50 ml of ethanol and allowed to react. The mixture was allowed to cool and then 4.0 g (9.8 mmol) of N-(2,6-dichloro-3-methylphenyl)-7-chloro-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide was added with stirring. After 15 minutes no starting material remained by thin layer chromatographic analysis although complete solution was never attained. The mixture was acidified with 6N hydrochloric acid and concentrated under reduced pressure. The residue was triturated with water and the solid removed by filtration and washed with water. It was then dissolved in aqueous sodium hydroxide using a minimum amount of the base and the aqueous solution was twice extracted with ether and acidified with 6N hydrochloric acid. The solid that formed was collected by filtration, washed with water, and dried. This was extracted with about 500 ml of boiling chloroform. The chloroform solution was concentrated to about 150 ml and allowed to cool to form a precipitate which was collected by filtration and dried to obtain 1.7 g (42 percent of theory) of the title compound as a white solid, m.p. 228°-9° C.

Workup

  1. customto react
  2. temperatureto cool
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with water
  5. customthe solid removed by filtration
  6. washwashed with water
  7. dissolutionIt was then dissolved in aqueous sodium hydroxide using a minimum amount of the base
  8. extractionthe aqueous solution was twice extracted with ether
  9. customThe solid that formed
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. customdried
  13. extractionThis was extracted with about 500 ml of boiling chloroform
  14. concentrationThe chloroform solution was concentrated to about 150 ml
  15. temperatureto cool
  16. customto form a precipitate which
  17. filtrationwas collected by filtration
  18. customdried

Sources & evidence

ORD record
ord-f2a0542e66e94da485e2976832b24498
Source dataset
uspto-grants-1990_09
Patent number
US04954163

Reaction notes

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