Water → 2-chloro-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-4-nitroaniline

HRID 56222

反応式

HRID 56222 の反応式
Cl.[CH3:2][C:3]([NH2:16])([CH3:15])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1F.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[CH:22][C:23]=1[NH:16][C:3]([CH3:2])([CH3:15])[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 532499312-Methyl-1-(naphthalen-2-yl)propan-2-amine--hydrogen chloride (1/1)

生成物 1

HCID 900236622-chloro-N-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)-4-nitroaniline収率 43%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
140 °C

実験手順

A mixture of 2-methyl-1-(naphthalen-2-yl)propan-2-amine hydrochloride (5.9 g, 25.0 mmol), 3-chloro-4-fluoro-1-nitrobenzene (5.27 g, 30.0 mmol) and K2CO3 (6.9 g, 50.0 mmol) in DMSO (50 mL) was stirred at 140° C. overnight. The mixture was cooled to rt and poured into 150 mL of water. The mixture was then extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/DCM (V/V)=10:1) to give the title compound as yellow foam (3.78 g, 43%).

後処理

  1. temperatureThe mixture was cooled to rt
  2. extractionThe mixture was then extracted with EtOAc (50 mL×3)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/DCM (V/V)=10:1)

出典と根拠

ORDレコード
ord-3950c11c8b84445db2e60821f7773461
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

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