Sodium Iodide → 3-Nonyloxy-benzenecarboxamide

HRID 415566

反応式

HRID 415566 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:19](Cl)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[CH:5]=[CH:6][CH:7]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 171851-ChlorononaneHCID 3424033-Hydroxybenzamide

生成物 1

HCID 445812983-Nonyloxy-benzenecarboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 3-hydroxybenzenecarboxamide (200 mg, 1.46 mmol, 1 equiv.) in DMF (3 ml) was added K2CO3 (302 mg, 2.19 mmol, 1.5 equiv.) and NaI (43.5 mg, 0.29 mmol, 0.2 equiv). The suspension was stirred for 5 min before n-nonyl chloride (0.32 ml, 1.61 mmol, 1.1 equiv) was introduced. The resulting mixture was warmed to 60° C. where it was maintained for 16 h. After this time, the reaction was cooled to room temperature and partitioned between EtOAc and water. The organic phase was separated, washed with additional water (×2), dried (MgSO4), filtered and concentrated in vacuo to reveal a colourless solid. In the case of 3-n-nonyloxybenzamide this colourless solid was stirred for 5 min with MeOH (˜0.5 ml) [NB: 3-n-nonyloxybenzamide partially soluble in MeOH] and then filtered to reveal the desired compound as a colourless solid (116 mg, 30%). HPLC-MS (method 3): m/z 264 [M+H]+, Rt=1.80 min. 1H NMR (d6-DMSO) δ=7.95 (s, 1H), 7.44-7.31 (m, 4H), 7.06 (ddd, J=8 Hz, J=2 Hz, J=1 Hz, 1H), 3.99 (t, J=6.5 Hz, 2H), 1.72 (quintet, J=6.5 Hz, 2H), 1.42 (m, 2H), 1.34-1.26 (m, 10H), 0.86 (t, J=6.5 Hz, 3H).

後処理

  1. additionwas introduced
  2. temperaturewas maintained for 16 h
  3. temperatureAfter this time, the reaction was cooled to room temperature
  4. custompartitioned between EtOAc and water
  5. customThe organic phase was separated
  6. washwashed with additional water (×2)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. filtration3-n-nonyloxybenzamide partially soluble in MeOH] and then filtered

出典と根拠

ORDレコード
ord-1d60744dd6ba4a768d71a4d2acda9810
出典データセット
uspto-grants-2012_01
特許番号
US08088791B2

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