Ethanol → 3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid ethyl ester

HRID 10278노트

반응식

HRID 10278 반응식
[CH2:1]([O:8][N:9]=[CH:10][C:11]1[C:12]([F:22])=[C:13]([CH:17]=[C:18]([F:21])[C:19]=1[F:20])[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](O)[CH3:24].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:23]([O:15][C:14](=[O:16])[C:13]1[CH:17]=[C:18]([F:21])[C:19]([F:20])=[C:11]([CH:10]=[N:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]=1[F:22])[CH3:24]

참가 물질

6

반응물 3

HCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 738573153-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid

생성물 1

HCID 737372813-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid ethyl ester수율 53.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (0.117 g, 0.378 mmol), 4-dimethylaminopyridine (0.023 g, 0.189 mmol), anhydrous ethanol (0.030 mL, 0.517 mmol) are mixed in dichloromethane (6 mL), cooled to 0° C., and treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.082 g, 0.427 mmol). After 2 hours at 0° C. and room temperature for 21 hours, the solvents are evaporated. The residue is dissolved in chloroform, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by chromatography (1:8 ethyl acetate/hexanes) provided the title compound (0.068 g). 1H NMR (200 MHz, CDCl3): δ 8.27 (s, 1H), 7.87–7.66 (m, 1H), 7.49–7.28 (m, 5H), 5.27 (s, 2H), 4.48–4.29 (q, 2H), 1.46–1.31 (t, 3H).

후처리

  1. waitroom temperature for 21 hours
  2. customthe solvents are evaporated
  3. dissolutionThe residue is dissolved in chloroform
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (1:8 ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-86eb074600d544ca8411b5312724ec9d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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