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

HRID 1764840

Reaction equation

HRID 1764840 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bd277ece4407459a83ebc0648c74a3be
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Linked notes

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