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

HRID 1914480

반응식

HRID 1914480 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

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

반응 조건

온도
137 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-71df0d2e04874968bc22261cfef1599d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614205B2

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