N,N'-Dimethylethylenediamine → 2,5-Dimethylbenzonitrile

HRID 2253501

反応式

HRID 2253501 の反応式
[C-]#N.[Na+].Br[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[CH3:12].[CH3:13][NH:14]CCNC.[OH-].[NH4+]>[Cu]I.O.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:12][C:6]1[CH:7]=[CH:8][C:9]([CH3:11])=[CH:10][C:5]=1[C:13]#[N:14]

参加物

9

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 8929Sodium CyanideHCID 11121Benzene, 2-bromo-1,4-dimethyl-HCID 14923Ammonium Hydroxide

生成物 1

HCID 836882,5-Dimethylbenzonitrile

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

An oven dried screw cap test tube was charged with NaCN (93 mg, 1.898 mmol), dried KI (52 mg, 0.313 mmol, 20 mol %) and CuI (30 mg, 0.158 mmol, 10 mol %), evacuated and backfilled with argon three times. 2-Bromo-1,4-dimethylbenzene (215 μL, 1.557 mmol), N,N′-dimethylethylenediamine (165 μL, 1.549 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was washed with 1 mL of water and dried over MgSO4. The GC analysis showed consumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS).

後処理

  1. customAn oven dried screw
  2. customcap test tube
  3. customevacuated
  4. customThe tube was sealed
  5. temperatureThe resulting yellow suspension was cooled to room temperature
  6. stirringThe mixture was stirred at 25° C. for 10 min
  7. washthe organic layer was washed with 1 mL of water
  8. dry with materialdried over MgSO4
  9. customconsumption of the majority of the starting material, and formation of the title compound (as confirmed by GC-MS)

出典と根拠

ORDレコード
ord-1478059c26de4e64809e19a5eef8769c
出典データセット
uspto-grants-2008_01
特許番号
US07323608B2

関連ノート

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