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

HRID 55077

반응식

HRID 55077 반응식
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]

참가 물질

6

반응물 3

HCID 70011-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

생성물 1

HCID 189716701-(4-Nitrophenylthio)naphthalene수율 35.5%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6d866d63b9524845b6be5c08298412a8
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624937

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