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

HRID 50964Notes

Reaction equation

HRID 50964 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 appararus. 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 appararus
  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-904e74b753614e24915791cedb72e393
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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