1,8-Diaminonaphthalene → 2,3-Dihydroperimidine

HRID 1768899

반응식

HRID 1768899 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.Cl[CH2:14]CCC(C1C=CC=CC=1)=O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[NH:1]1[C:2]2=[C:11]3[C:6](=[CH:5][CH:4]=[CH:3]2)[CH:7]=[CH:8][CH:9]=[C:10]3[NH:12][CH2:14]1

참가 물질

5

반응물 2

HCID 680671,8-DiaminonaphthaleneHCID 2535334-Chlorobutyrophenone

생성물 1

HCID 124409652,3-Dihydroperimidine수율 47.4%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140Toluene용매

실험 절차

A stirred mixture of 1.411 g of 1,8-diaminonaphthalene, 1.629 g of 4-chlorobutyro-phenone, 3 mg of p-toluenesulfonic acid monohydrate, and 10 mL of toluene was heated to reflux under a nitrogen atmosphere using a Dean-Stark trap to remove the water evolved from the reaction for 10 hr. The mixture was filtered to remove unreacted starting material, partioned between ethyl acetate and 5% sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 2.04 g of crude product. This was further purified by chromatography on silica gel, eluting with 1:1 diethyl ether/petroleum ether, and collecting the initial band to yield 0.719 g of dihydroperimidine intermediate.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. customto remove the water
  4. customevolved from the reaction for 10 hr
  5. filtrationThe mixture was filtered
  6. customto remove unreacted
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give 2.04 g of crude product
  11. customThis was further purified by chromatography on silica gel
  12. washeluting with 1:1 diethyl ether/petroleum ether
  13. customcollecting the initial band

출처 및 근거

ORD 기록
ord-0afe8927cbfd4921aeee83560246b418
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380635

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