Formamidine acetate → 6-[(4-Chlorophenyl)-(1,2,4-triazol-1-yl)methyl]-1-methylbenzotriazole

HRID 1376823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376823
[ClH:1].ClC1C=C[C:6]([NH:9][NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=CC=1.[C:22](O)(=O)[CH3:23].[CH:26](=[NH:28])N>CO>[Cl:1][C:22]1[CH:23]=[CH:16][C:21]([CH:11]([N:10]2[CH:26]=[N:28][CH:6]=[N:9]2)[C:12]2[CH:13]=[CH:14][C:15]3[N:19]=[N:18][N:17]([CH3:20])[C:16]=3[CH:21]=2)=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 160693Formamidine acetateHCID 18924324(+)-6-[(4-chlorophenyl)hydrazinomethyl]-1-methyl-1H-benzotriazole monohydrochloride

Produkt 1

HCID 607966-[(4-Chlorophenyl)-(1,2,4-triazol-1-yl)methyl]-1-methylbenzotriazoleAusbeute 131,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 5 g of intermediate 4-a, 4.8 g of methanimidamide monoacetate and 15 ml of methanol was stirred for 1.5 hours at reflux temperature. After cooling to room temperature, the reaction mixture crystallized and there were added 30 ml of water. After stirring for 1 hour the precipitate was filtered off, washed with water and dried in vacuo at 50° C. The product was diluted with 11.8 ml of 2-propanol and the whole was treated with active charcoal for 15 min. at reflux temperature. The charcoal was filtered off while hot and washed with 2-propanol. The product was crystallized, filtered off and dried in vacuo at 50° C., yielding 3.3 g (66.0%) of (+)-6-[(4-chlorophenyl)-(1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole (comp. 1-a); mp. 130°-135° C.; [α]D20 =+8.0° (conc.=10% in CH3OH); enantiomeric excess: 98.4%.

Aufarbeitung

  1. temperatureat reflux temperature
  2. customthe reaction mixture crystallized
  3. additionthere were added 30 ml of water
  4. stirringAfter stirring for 1 hour the precipitate
  5. filtrationwas filtered off
  6. washwashed with water
  7. customdried in vacuo at 50° C
  8. additionThe product was diluted with 11.8 ml of 2-propanol
  9. additionthe whole was treated with active charcoal for 15 min.
  10. temperatureat reflux temperature
  11. filtrationThe charcoal was filtered off while hot and
  12. washwashed with 2-propanol
  13. customThe product was crystallized
  14. filtrationfiltered off
  15. customdried in vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-ec000bd974d24d0198bd8f7632827eab
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663354

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