تفاعل #1004427

معادلة التفاعل

2,5-dichloro-N′-[4-(octyloxy)benzoyl]benzohydrazide

p-anisidine

Phosphorus trichloride

→

3-(2,5-dichlorophenyl)-4-(4-methoxyphenyl)-5-[4-(octyloxy)phenyl]-4H-1,2,4-triazole

المردود 34.0%

المذيبات

1,2-dichlorobenzene

ظروف التفاعل

المعالجة

1. 1
   أخرىInto a 1 L round-bottomed flask fitted with a mechanical stirrer
2. 2
   درجة الحرارةreflux condenser and nitrogen inlet
3. 3
   أخرىresulted in partial solvation of the solids
4. 4
   workup.DISTILLATIONThe solvent was distilled off under a light vacuum
5. 5
   أخرىthe residue transferred to a 2 L flask with 1 L of a 1:1 acetone/heptane mixture
6. 6
   ترشيحThe solid material was filtered off
7. 7
   workup.DISSOLUTIONdissolved in acetone
8. 8
   workup.ADDITIONEnough heptane was added
9. 9
   أخرىto precipitate a purple-colored oily sludge
10. 10
    أخرىhad been completely precipitated
11. 11
    أخرىThe acetone/heptane layer was decanted off
12. 12
    workup.ADDITIONdiluted further with a large excess of heptane
13. 13
    أخرىto precipitate a white solid
14. 14
    ترشيحThis was filtered off
15. 15
    workup.DISSOLUTIONdissolved in acetone
16. 16
    أخرىre-precipitated with heptane
17. 17
    ترشيحFiltration
18. 18
    أخرىdrying

الإجراء التجريبي

Into a 1 L round-bottomed flask fitted with a mechanical stirrer, reflux condenser and nitrogen inlet were introduced 2,5-dichloro-N′-[4-(octyloxy)benzoyl]benzohydrazide (40 g, 0.09146 mole, 1 equivalent), p-anisidine (67.60 g, 0.5487 mole, 6 equivalents) and 300 mL 1,2-dichlorobenzene. Mechanical stirring resulted in partial solvation of the solids. Phosphorus trichloride (12.56 g, 0.0146 mole, 1 equivalent) was added and the contents of the flask heated at 180° C. for 12 hrs. The solvent was distilled off under a light vacuum and the residue transferred to a 2 L flask with 1 L of a 1:1 acetone/heptane mixture. The solid material was filtered off and dissolved in acetone. Enough heptane was added to precipitate a purple-colored oily sludge. Heptane dilution of a test sample of the acetone/heptane layer ensured that the oily sludge had been completely precipitated. The acetone/heptane layer was decanted off and diluted further with a large excess of heptane to precipitate a white solid. This was filtered off, dissolved in acetone and re-precipitated with heptane. Filtration and drying gave 3-(2,5-dichlorophenyl)-4-(4-methoxyphenyl)-5-[4-(octyloxy)phenyl]-4H-1,2,4-triazole (16.25 g, 34% yield).

المصدر