(2-Chloro-6-nitrophenyl)(3-chloropropyl)sulfane → 3-Chloro-2-[(3-chloropropyl)sulfanyl]aniline

HRID 1764840

반응식

HRID 1764840 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[S:11][CH2:12][CH2:13][CH2:14][Cl:15]>CO>[Cl:1][C:2]1[C:3]([S:11][CH2:12][CH2:13][CH2:14][Cl:15])=[C:4]([CH:5]=[CH:6][CH:7]=1)[NH2:8]

참가 물질

3

반응물 1

HCID 22735865(2-Chloro-6-nitrophenyl)(3-chloropropyl)sulfane

생성물 1

HCID 227355373-Chloro-2-[(3-chloropropyl)sulfanyl]aniline수율 93%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The crude 1-chloro-2-[(3-chloropropyl)sulfanyl]-3-nitrobenzene was dissolved in MeOH (150 mL) and degassed with N2. Palladium hydroxide (1.8 g) was added in four portions to this solution in a Parr apparatus. The resulting heterogeneous solution was shaken under hydrogenation conditions (55 psi) at room temp for 18 h. The catalyst was removed via filtration in the same manner as above and the filtrate was concentrated in vacuo. to afford 3-chloro-2-[(3-chloropropyl)sulfanyl]aniline (9.94 g, 93%) as a dark oil: 1H NMR (CHCl3, 300 MHz) δ7.03 (t, 1H, J=8.1 Hz), 6.82 (t, 1H, J=8.1 Hz), 6.63 (t, 1H, J=8.0 Hz), 4.62 (br s, 1H), 3.68 (t, 2H, J=6.4 Hz), 2.92 (t, 2H, J=6.9 Hz), 1.98 (quintet, 2H, J=6.6 Hz) ppm.

후처리

  1. customdegassed with N2
  2. additionPalladium hydroxide (1.8 g) was added in four portions to this solution in a Parr apparatus
  3. customThe catalyst was removed via filtration in the same manner as above and the filtrate
  4. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-bd277ece4407459a83ebc0648c74a3be
출처 데이터셋
uspto-grants-2007_06
특허 번호
USRE039679E1

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