P-Anisidine → 3-(2,5-Dichlorophenyl)-4-(4-methoxyphenyl)-5-[4-(octyloxy)phenyl]-4H-1,2,4-triazole

HRID 2118373

反応式

HRID 2118373 の反応式
[Cl:1][C:2]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:3]=1[C:4]([NH:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][CH:10]=1)=O.[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1.P(Cl)(Cl)Cl>ClC1C=CC=CC=1Cl>[Cl:1][C:2]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:3]=1[C:4]1[N:38]([C:35]2[CH:36]=[CH:37][C:32]([O:31][CH3:30])=[CH:33][CH:34]=2)[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:11][CH:10]=2)=[N:7][N:6]=1

参加物

5

反応物 3

HCID 7732P-AnisidineHCID 24387Phosphorus trichlorideHCID 219820862,5-dichloro-N'-[4-(octyloxy)benzoyl]benzohydrazide

生成物 1

HCID 219821043-(2,5-Dichlorophenyl)-4-(4-methoxyphenyl)-5-[4-(octyloxy)phenyl]-4H-1,2,4-triazole収率 34%

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

反応条件

温度
180 °C

実験手順

Into a 1L 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 (8) (16.25 g, 34% yield).

後処理

  1. temperaturereflux condenser and nitrogen inlet
  2. customresulted in partial solvation of the solids
  3. distillationThe solvent was distilled off under a light vacuum
  4. customthe residue transferred to a 2 L flask with 1 L of a 1:1 acetone/heptane mixture
  5. filtrationThe solid material was filtered off
  6. dissolutiondissolved in acetone
  7. additionEnough heptane was added
  8. customto precipitate a purple-colored oily sludge
  9. customhad been completely precipitated
  10. customThe acetone/heptane layer was decanted off
  11. additiondiluted further with a large excess of heptane
  12. customto precipitate a white solid
  13. filtrationThis was filtered off
  14. dissolutiondissolved in acetone
  15. customre-precipitated with heptane
  16. filtrationFiltration
  17. customdrying

出典と根拠

ORDレコード
ord-10c2ee2a0dc540cd9929cf87e5620731
出典データセット
uspto-grants-2008_10
特許番号
US07442760B2

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