4-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene → 4-(3,5-Dimethyl-benzylsulfanyl)-phenylamine

HRID 855994ノート

反応式

HRID 855994 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>O.C(O)C.[Fe]>[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH2:5][S:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[CH:11][CH:12]=1

参加物

5

反応物 1

HCID 694205454-(3,5-Dimethyl-benzylsulfanyl)-nitrobenzene

生成物 1

HCID 432993384-(3,5-Dimethyl-benzylsulfanyl)-phenylamine収率 93.1%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A mixture of 4-(3,5-dimethyl-benzylsulfanyl)-nitrobenzene (0.35 g, 1.28 mmol) calcium chloride (0.071 g, 0.64 mmol) and iron powder (−325 mesh) (0.573 g, 10.3 mmol) in 4 ml water and 17 ml ethanol was heated at reflux under nitrogen for 4.5 h. The reaction mixture was then cooled to room temperature, filtered through Celite and the filtrate was concentrated under reduced pressure. The residual oil was purified by column chromatography, eluting with 9:1 hexane/ethyl acetate to yield the title compound as a yellowish oil (0.29 g, 91% yield). MS: 244.3 (M+1)

後処理

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 4.5 h
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residual oil was purified by column chromatography
  6. washeluting with 9:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-fa9e83e4ee6544528f789f601c7bcb73
出典データセット
uspto-grants-2007_08
特許番号
US07262318B2

反応ノート

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