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

HRID 1288622Notes

Reaction equation

HRID 1288622 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 607966-[(4-Chlorophenyl)-(1,2,4-triazol-1-yl)methyl]-1-methylbenzotriazoleYield 131.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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-chloro-phenyl)-(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%.

Workup

  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.

Sources & evidence

ORD record
ord-72596471c56a4c07b7617d5e855a6df5
Source dataset
uspto-grants-1998_05
Patent number
US05746840

Reaction notes

Loading…