Salicylic Acid → N-(2-chloro-4-nitrophenyl)-2 hydroxybenzamide

HRID 1509833

反応式

HRID 1509833 の反応式
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Cl:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH2:14].P(Cl)(Cl)Cl.ClCCl>>[Cl:11][C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH:14][C:1](=[O:10])[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4]

参加物

5

反応物 4

HCID 338Salicylic AcidHCID 6344DichloromethaneHCID 84922-Chloro-4-nitroanilineHCID 24387Phosphorus trichloride

生成物 1

HCID 2844786N-(2-chloro-4-nitrophenyl)-2 hydroxybenzamide

反応条件

温度
137 °C

実験手順

The method disclosed in U.S. Pat. No. 3,079,297 to Shraufstatter et al with minor variations was utilized. A boiling solution of salicylic acid (1.03 g, 7.46 mmol) and 2-chloro-4-nitroaniline (1.29 g, 7.46 mmol) in xylenes (20 mL) was treated dropwise with a solution of phosphorous trichloride in dichloromethane 2.0M, 1.50 mL, 0.40 equiv.), and the resulting solution was refluxed (137° C.) for four hours. The solution was cooled to about 125° C. An oily residue covered the bottom and sides of the reaction vessel. The hot reaction solution was transferred by glass pipette to a beaker and was allowed to cool to room temperature while being stirred rapidly. The product separated, was collected by filtration, and washed with hexanes, then recrystallized from ethanol. The title compound was obtained, MP 218-220° C. (dec.). 1HNMR (500 MHz, DMSO-d6): δ 7.02 (m, 1H, H3), 7.07 (m, 1H, H5), 7.49 (m, 1H, H4), 8.04 (m, 1H, H6), 8.28 (m, 1H, H5′), 8.41 (m, 1H, H3′), 8.85 (m, 1H, H6′), 11.8 (s, 1H, NH), 12.34 (s, 1H, OH).

後処理

  1. temperatureThe solution was cooled to about 125° C
  2. temperatureto cool to room temperature
  3. customThe product separated
  4. filtrationwas collected by filtration
  5. washwashed with hexanes
  6. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-f7371c5d6ddf4995b96f3264db1f0942
出典データセット
uspto-grants-2012_07
特許番号
US08211882B2

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