HCID 22735649、化合物 → 5-Bromo-2-[(3-chloropropyl)sulfanyl]aniline

HRID 50971ノート

反応式

HRID 50971 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][Cl:12])=[C:4]([N+:13]([O-])=O)[CH:3]=1>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][Cl:12])=[C:4]([CH:3]=1)[NH2:13]

参加物

3

反応物 1

HCID 22735649HCID 22735649、化合物

生成物 1

HCID 227357605-Bromo-2-[(3-chloropropyl)sulfanyl]aniline収率 73%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Bromo-1-[(3-chloropropyl)sulfanyl]-2-nitrobenzene (1.97 g, 7.1 mmol) was dissolved in MeOH (25 mL). The reaction flask was evacuated with nitrogen, and Pd(OH)2 on carbon (400 mg) was added. The reaction flask was evacuated with nitrogen several time before being subjected to an atmosphere of H2 (50 psi). The flask was shaken on a parr apparatus for 72 hrs. The reaction was filtered over a bed of celite and the residue was washed with MeOH (5 mL). The supernant was concentrated, and the crude, balck residue was purified by column chromatography (50-20% hexanes-CH2Cl2), to afford 5-bromo-2-[(3-chloropropyl)sulfanyl]aniline (1.28 g, 73%) as a clear oil. 1H NMR (CDCl3, 300 Mhz) δ7.20 (d, 1H, 8.0 Hz), 6.88 (d, 1H, 2.0 Hz), 6.79 (dd, 1H, 2.0 Hz, 8.0 Hz), 4.41 (s, 2H), 3.64 (t, 2H, 6.6 Hz), 2.86 (t, 2H, 7.0 Hz), 1.94-1.99 (m, 2H) ppm.

後処理

  1. customThe reaction flask was evacuated with nitrogen, and Pd(OH)2 on carbon (400 mg)
  2. additionwas added
  3. customThe reaction flask was evacuated with nitrogen several time
  4. filtrationThe reaction was filtered over a bed of celite
  5. washthe residue was washed with MeOH (5 mL)
  6. concentrationThe supernant was concentrated
  7. customthe crude, balck residue was purified by column chromatography (50-20% hexanes-CH2Cl2)

出典と根拠

ORDレコード
ord-9de867f0fe5a4143af43a955f851091f
出典データセット
uspto-grants-2004_03
特許番号
US06713471B1

反応ノート

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