p-Toluidine → 3,5-Dimethyl-N-(4-methylphenyl)benzenamine

HRID 1883455ノート

反応式

HRID 1883455 の反応式
C(N(CC)C(=O)C1C(=CC=CC=1)O)C.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1.[OH-].[NH4+].CCCCCCCCCCCC>[Cu]I.O.C(OCC)(=O)C>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:32]2[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=2)=[CH:17][CH:18]=1

参加物

10

反応物 6

HCID 7813p-ToluidineHCID 8182DodecaneHCID 14923Ammonium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 88006DiethylsalicylamideHCID 136357Benzene, 1-bromo-3,5-dimethyl-2 回

生成物 1

HCID 98131563,5-Dimethyl-N-(4-methylphenyl)benzenamine

試薬・触媒・溶媒 3

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

反応条件

温度
100 °C

実験手順

CuI (10 mg, 0.05 mmol), N,N-diethylsalicylamide (10 mg, 0.05 mmol), 4-toluidine (161, 1.5 mmol) and K3PO4 (425 mg, 2.0 mmol) were put into a screw-capped test tube with a Teflon-lined septum. The tube was then evacuated and backfilled with argon (3 cycles). 5-Bromo-m-xylene (136 μL, 1.0 mmol) was added by a syringe. The reaction mixture was stirred at 100° C. for 20 h. The reaction mixture was allowed to reach room temperature. Ethyl acetate (˜2 mL), water (˜10 mL), ammonium hydroxide (˜0.5 mL) and dodecane (227 μL) were added. The organic phase was analyzed by GC and 22% conversion of 5-bromo-m-xylene and 9% GC yield of the desired product was obtained.

後処理

  1. customThe tube was then evacuated
  2. customto reach room temperature

出典と根拠

ORDレコード
ord-08da84d60abb4928aa2eb9e7ff7c3b74
出典データセット
uspto-grants-2004_07
特許番号
US06759554B2

反応ノート

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