Hydrochloric Acid → N-dodecyl-3,5-bis(m-trifluoromethylphenyl)4-(2-hydroxyethoxy)benzamide

HRID 324051노트

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HRID 324051 반응식
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Li]CCCC.C([O:21][C:22](=O)[C:23]1[CH:28]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[C:26]([O:39][CH2:40][CH2:41][OH:42])=[C:25]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:52])([F:51])[F:50])[CH:44]=2)[CH:24]=1)C.Cl>C1COCC1>[CH2:1]([NH:13][C:22](=[O:21])[C:23]1[CH:24]=[C:25]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([C:49]([F:51])([F:52])[F:50])[CH:44]=2)[C:26]([O:39][CH2:40][CH2:41][OH:42])=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([C:35]([F:38])([F:37])[F:36])[CH:30]=2)[CH:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 13583DodecylamineHCID 540981933,5-Bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)benzoic acid ethyl esterHCID 178418339Butyllithium

생성물 1

HCID 22237575N-dodecyl-3,5-bis(m-trifluoromethylphenyl)4-(2-hydroxyethoxy)benzamide수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a flame-dried flask containing dodecyl amine (0.278 g, 1.5 mmol) in THF (5 mL) cooled to −78° C. was added n-BuLi (titrated to 2.37 M in hexanes) (0.670 mL, 1.59 mmol) dropwise. The solution was stirred at −78° C. for 20 min. and then warmed to room temperature over 20 min. The reaction was then recooled to −40° C. and 3,5-bis-(m-trifluoromethylphenyl)4-(2-hydroxyethoxy)benzoic acid ethyl ester (0.215 g, 0.43 mmol) in THF (5 mL) was added. This mixture was allowed to warm to room, temperature over 20 min. The reaction mixture was then poured into 0.1 N HCl solution and extracted with EtOAc. The combined organic layers were washed with 2 N HCl solution (3×), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (30% EtOAc:hexane) to afford N-dodecyl-3,5-bis(m-trifluoromethylphenyl)-4-(2-hydroxyethoxy)benzamide (0.254 g, 93%) as a white solid. 1H NMR (CDCl3) δ7.90 (m, 2H); 7.82-7.76 (m, 4H); 7.65-7.56 (m, 4H); 6.22 (bt, 1H); 3.45 (dd, 2H); 3.30 (m, 4H); 1.60 (m, 2H); 1.25 (m, 18H); 0.84 (m, 3H).

후처리

  1. temperaturewarmed to room temperature over 20 min
  2. customwas then recooled to −40° C.
  3. temperatureto warm to room, temperature over 20 min
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with 2 N HCl solution (3×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (30% EtOAc:hexane)

출처 및 근거

ORD 기록
ord-d586ff4e98ed4d87a6e215a7f3f7ba5f
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06214877B1

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