1-Bromonaphthalene → 1-(4-Nitrophenylthio)naphthalene

HRID 55077

反応式

HRID 55077 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

参加物

6

反応物 3

HCID 70011-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

生成物 1

HCID 189716701-(4-Nitrophenylthio)naphthalene収率 35.5%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 1049Pyridine溶媒

実験手順

1-Bromonaphthalene (0.15 mole, 31.0 g),4-nitrothiophenol 0.11 mole, 17.0 g), potassium carbonate (0.15 moles, 20.7 g), copper bronze (0.3 moles, 18.9 g) and cuprous chloride (0.06 moles, 6.0 g) were refluxed in 500 ml pyridine for 3 days. The reaction was filtered while hot, and then concentrated. Ethyl acetate was added and the solution washed with water and 5N HCl, dried over sodium sulfate and concentrated. The product was purified twice by HPLC over silica gel eluted with 20% ethyl acetate/hexane followed by 5 ethyl acetate/hexane to yield 1-(4-nitrophenylthio)naphthalene 11.0 g, 26%. Mass Spec (FD) 282. Calculated for C16H11NO2S: C, 68.31 H, 3.94, N, 4.98. Found: C, 68.52; H, 4.00; N, 4.77.

後処理

  1. filtrationThe reaction was filtered while hot, and
  2. concentrationthen concentrated
  3. additionEthyl acetate was added
  4. washthe solution washed with water and 5N HCl
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified twice by HPLC over silica gel
  8. washeluted with 20% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-6d866d63b9524845b6be5c08298412a8
出典データセット
uspto-grants-1997_04
特許番号
US05624937

関連ノート

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