Hydrochloric Acid → 3-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol

HRID 1004394ノート

反応式

HRID 1004394 の反応式
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[CH:10][C:9]([NH:12]N)=[CH:8][CH:7]=2)[CH:5]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.Cl>O1CCOCC1>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:11]=[C:10]3[C:9](=[CH:8][CH:7]=2)[NH:12][CH:19]=[C:18]3[CH2:17][CH2:16][CH2:15][OH:14])[CH:5]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 80803,4-dihydro-2H-pyranHCID 51624184-(4-hydrazinylphenyl)-4H-1,2,4-triazole

生成物 1

HCID 106339143-[5-(1,2,4-triazol-4-yl)-1H-indol-3-yl]propan-1-ol収率 30%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A solution of 4-(1,2,4-triazol-4yl)phenylhydrazine (25 g, 143 mmol) in dioxan (250 ml) was treated with dihydropyran (24 g, 286 mmol) followed by 1M hydrochloric acid (150 ml) and heated at reflux for 18 h. The reaction mixture was evaporated, treated with toluene the re-evaporated. Inorganic solids were removed by treating the residue with a mixture of methanol and acetonitrile. The mother liquors were purified by column chromatography on silica using dichloromethane/methanol (9:1→4:1) as the eluant. The compound was recrystallised from acetonitrile to afford the title compound as a colourless solid (10.24 g, 30%); mp 205-207° C. (Found: C, 64.37; H, 5.76; N, 22.83. C13H14N4O requires: C, 64.45; H, 5.82; N, 23.13%.) δH (360 MHz, DMSO-d6) 1.81 (2H, q, J=7 Hz, CH2), 2.75 (2H, t, J=8 Hz, CH2), 3.46 (2H, dt, J1 =6, J2 =5 Hz, CH2), 4.43 (1H, t, J=5 Hz, OH), 7.26 (1H, d, J=2 Hz, Ar-H), 7.29 (1H, dd, J1 =9, J2 =2 Hz, Ar-H), 7.47 (1H, d, J=9 Hz, Ar-H), 7.77 (1H, d, J=2 Hz, Ar-H), 9.01 (2H, s, triazole-H), 11.05 (1H, br s, indole NH); m/z (CI) 243 (M+ +1)

後処理

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. customThe reaction mixture was evaporated
  4. additiontreated with toluene the re-evaporated
  5. customInorganic solids were removed
  6. additionby treating the residue
  7. additionwith a mixture of methanol and acetonitrile
  8. customThe mother liquors were purified by column chromatography on silica
  9. customThe compound was recrystallised from acetonitrile

出典と根拠

ORDレコード
ord-eb7efde034a94decaabc8abeec8acc7a
出典データセット
uspto-grants-2000_04
特許番号
US06048878

反応ノート

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