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Pyridine → 5,7-dimethyl-N-(2-acetoxymethyl-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide

HRID 477239
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 477239
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:7]=1[NH2:13])(=[O:3])[CH3:2].N1C=CC=CC=1.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]2[N:28]=[C:29]([S:31](Cl)(=[O:33])=[O:32])[N:30]=[C:23]2[N:22]=1.S(Cl)(Cl)(=O)=O.[OH-].[Na+]>C(Cl)Cl.C(#N)C>[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[N:24]2[N:28]=[C:29]([S:31]([NH:13][C:7]3[C:8]([Cl:12])=[CH:9][CH:10]=[CH:11][C:6]=3[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:32])=[O:33])[N:30]=[C:23]2[N:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 6112325,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonyl chlorideHCID 141554092-Acetoxymethyl-6-chloroaniline

Produkt 1

HCID 14155203
5,7-dimethyl-N-(2-acetoxymethyl-6-chlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide
Ausbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of 1.30 gm (6.50 mmol) of 2-amino-3-chlorobenzyl acetate, 4.11 gm (52.0 mmol) of pyridine and 5.0 ml of acetonitrile was treated with 1.61 gm (6.50 mmol) of 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride and the resulting mixture stirred at 25° C. for 120 hours. An additional 0.53 gm (2.2 mmol) of the sulfonyl chloride was added and stirring at 25° C. continued for an additional 24 hours. The mixture was filtered and the filtrate evaporated to provide a brown oil. The oil was then dissolved in 40 ml of methylene chloride and stirred with 25 ml of 0.5M NaOH. After 5 minutes, the aqueous phase was separated, washed with ether and acidified with 3N HCl. A light brown solid was collected, washed with water, dried and recrystallized from acetonitrile to provide 0.35 gm (13%) of the desired product as a solid, mp 214° -217° C., containing approximately 10% of an impurity. IR and 1H NMR spectra were in agreement with the assigned structure.

Aufarbeitung

  1. stirringstirring at 25° C.
  2. waitcontinued for an additional 24 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated
  5. customto provide a brown oil
  6. waitAfter 5 minutes
  7. customthe aqueous phase was separated
  8. washwashed with ether
  9. customA light brown solid was collected
  10. washwashed with water
  11. customdried
  12. customrecrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-86025e4e28da467fa5fdef7728dfd7a7
Quelldatensatz
uspto-grants-1989_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04886883

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