4-Methyl-3-nitroaniline → N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

HRID 273292

反応式

HRID 273292 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[CH3:11])[NH2:7])([O-:3])=[O:2].C([Al](CC(C)C)CC(C)C)C(C)C.C[O:26][C:27](=O)[C:28]1[CH:33]=[CH:32][C:31]([CH2:34][N:35]2[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]2)=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[CH3:11][C:10]1[CH:9]=[CH:8][C:6]([NH:7][C:27](=[O:26])[C:28]2[CH:29]=[CH:30][C:31]([CH2:34][N:35]3[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)=[CH:32][CH:33]=2)=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

参加物

5

反応物 3

HCID 83904-Methyl-3-nitroanilineHCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateHCID 16682931Triisobutylaluminum2 回

生成物 1

HCID 29984087N-(4-Methyl-3-nitro-phenyl)-4-(4-methyl-piperazin-1-ylmethyl)-benzamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a solution of 10.95 g (72 mmol) of 3-nitro-4-methyl-aniline in 80 ml of toluene is added a solution of triisobutylaluminium (28% in hexane), 66.5 ml (61 mmol) over a period of 30 min at 0° C. followed by the addition of a solution of 4-(4-methyl-piperazin-1-ylmethyl)-benzoic acid methyl ester (14.9 g, 60 mmol) in toluene (30 ml) during 1 hour at 0° C. under an atmosphere of argon. After stirring for 12 h at room temperature an other portion of triisobutylaluminium (66.5 ml (61 mmol) is added to the dark brown reaction mixture. The mixture is stirred for additional 6 h, then 2 additional small portions of triusobutylaluminium (each 18 ml, 18 mmol) are added and stirring is continued for several hours at room temperature. After acidic and basic workup with sulfuric acid and NaOH the combined organic toluene phases are evaporated in vacuo to give a brown crude product which was crystallized from t-butyl methyl ether to give the title compound as brownish yellow crystals: first crop (11.65 g), sec. crop (3.8 g) and a third crop (1.2 g). in summary 16.65 g (75.3%).

後処理

  1. additionis added to the dark brown reaction mixture
  2. addition2 additional small portions of triusobutylaluminium (each 18 ml, 18 mmol) are added
  3. stirringstirring
  4. waitis continued for several hours at room temperature
  5. customAfter acidic and basic workup with sulfuric acid and NaOH the combined organic toluene phases are evaporated in vacuo
  6. customto give a brown crude product which
  7. customwas crystallized from t-butyl methyl ether

出典と根拠

ORDレコード
ord-a722b3bc9e9a4f0d980f2a5de88b26f2
出典データセット
uspto-grants-2008_11
特許番号
US07456283B2

関連ノート

読み込み中…