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

HRID 50964

反応式

HRID 50964 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-904e74b753614e24915791cedb72e393
出典データセット
uspto-grants-2004_03
特許番号
US06713471B1

関連ノート

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