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

HRID 16184노트

반응식

HRID 16184 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
40 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-bf03f142048549069bc2478ad7d6db48
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737136B2

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