Dimethylformamide → Aniline, p-isopropyl-N-methyl-

HRID 594815

反応式

HRID 594815 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.CN.CC([O-])=O.[K+].[CH3:18][N:19](C=O)C>O.[Cu]I>[CH3:18][NH:19][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 114621-Bromo-4-isopropylbenzeneHCID 517044Potassium Acetate

生成物 1

HCID 138880Aniline, p-isopropyl-N-methyl-収率 34%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 1-bromo-4-isopropylbenzene (1.0 g, 5.03 mmol), methylamine (25 mL, 50.0 mmol), CuI (1.15 g, 6.0 mmol), KOAc (1.24 g, 12.6 mmol) and DMF (30 mL) in a sealed tube under N2 was heated to 100° C. overnight. The mixture was cooled to r.t., diluted with water (100 mL), and extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated, and purified by silica gel chromatography (PE:EtOAc=10:1) to give 254 mg (34%) of the title compound as a yellow oil. [M+H] Calc'd for C10H15N, 150. Found, 150.

後処理

  1. temperatureThe mixture was cooled to r.t.
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (PE:EtOAc=10:1)

出典と根拠

ORDレコード
ord-3e16f4e465e840d68cec29f74c2d0697
出典データセット
uspto-grants-2016_01
特許番号
US09242968B2

関連ノート

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