Stannous chloride dihydrate → 4-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine

HRID 16184ノート

反応式

HRID 16184 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:4]([N+:16]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 214144194-Chloro-N-methyl-2-nitro-N-phenylphenylamine

生成物 1

HCID 167750454-Chloro-N1-methyl-N1-phenylbenzene-1,2-diamine収率 87%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
40 °C

実験手順

To a solution of 4-chloro-N-methyl-2-nitro-N-phenylphenylamine (12.5 g, 46.3 mmol) in ethanol (250 mL) was added SnCl2.2H2O (37.5 gr., 0.17 mol). The solution was heated to 40° C. and stirred for 6 h. The reaction mixture was concentrated in vacuo and subsequently diluted with ethyl acetate (500 mL) and washed with H 20 (500 mL), a cooled (0° C.) aq. solution of NaOH (1 M, 200 mL), H2O (500 mL) and brine (500 mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced presssure. The crude compound was applied onto a silica column and eluted with heptane/ethyl acetate (8/2, v/v) affording the title compound (9.3 g, 87% yield). Data: Rf 0.65 (heptane/ethyl acetate, 7/3, v/v), (m/z)=233 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionsubsequently diluted with ethyl acetate (500 mL)
  3. washwashed with H 20 (500 mL)
  4. temperaturea cooled (0° C.) aq. solution of NaOH (1 M, 200 mL), H2O (500 mL) and brine (500 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced presssure
  8. washeluted with heptane/ethyl acetate (8/2

出典と根拠

ORDレコード
ord-bf03f142048549069bc2478ad7d6db48
出典データセット
uspto-grants-2010_06
特許番号
US07737136B2

反応ノート

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