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

HRID 10278ノート

反応式

HRID 10278 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-86eb074600d544ca8411b5312724ec9d
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

反応ノート

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