Calcium Chloride → 4-methoxy-N1,N1-bis-(4-methyl-benzyl)-benzene-1,3-diamine

HRID 51861

反応式

HRID 51861 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[N+:26]([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[NH2:26]

参加物

5

反応物 2

HCID 5284359Calcium ChlorideHCID 22736971(4-Methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amine

生成物 1

HCID 227369664-methoxy-N1,N1-bis-(4-methyl-benzyl)-benzene-1,3-diamine収率 91.1%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of 500 mg (1.33 mmol) (4-methoxy-3-nitro-phenyl)-bis-(4-methyl-benzyl)-amine in 20 ml ethanol at room temperature were added 1.91 g (29.2 mmol) zinc powder and 147 mg (1.33 mmol) calcium chloride and the mixture was then heated at 90° C. for 16 hours. The mixture was then filtered and the filtrate diluted with ethyl acetate and washed with 0.5 N sodium hydroxide solution and then with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford 420 mg (91%) 4-methoxy-N1,N1-bis-(4-methyl-benzyl)-benzene-1,3-diamine as a dark brown oil. ES-MS m/e (%): 347 (M+H+, 100).

後処理

  1. filtrationThe mixture was then filtered
  2. additionthe filtrate diluted with ethyl acetate
  3. washwashed with 0.5 N sodium hydroxide solution
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bb3f0eeaebb04945a0a5661a68669b85
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

関連ノート

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