Ethylene Glycol → 3',4'-Dihydro-2'-(1H-1,2,4-Triazol-1-yl)-Spiro-[1,3-Dioxolane-2,1'(2'H)-Naphthalene]

HRID 2165989노트

반응식

HRID 2165989 반응식
[N:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH:5]=[N:4][CH:3]=[N:2]1.[CH2:17](O)[CH2:18][OH:19].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>ClCCl.C(O)CCC>[N:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]32[O:19][CH2:18][CH2:17][O:16]3)[CH:5]=[N:4][CH:3]=[N:2]1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 146988003,4-Dihydro-2-(1H-1,2,4-triazole-1-yl)1(2H)-Naphthalenone

생성물 1

HCID 197619943',4'-Dihydro-2'-(1H-1,2,4-Triazol-1-yl)-Spiro-[1,3-Dioxolane-2,1'(2'H)-Naphthalene]

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 10 g. 3,4-dihydro-2-(1H-1,2,4-triazol-1-yl)-1-(2H)-naphthalenone, 5.8 g. ethylene glycol and 11.5 g. p-toluenesulfonic acid was refluxed in a mixed solvent of 150 ml. toluene and 70 ml. n-butanol under a Dean-Stark [trademark] trap for 48 hours. The solvent was evaporated leaving a slurry which was taken up in dichloromethane and washed twice with 10% aqueous sodium hydroxide and once with water. The extract was dried in sodium sulfate, filtered and evaporated leaving an oily residue which crystallized on cooling to yield 1.5 g. of white crystals. These white crystals were 3',4'-dihydro-2'-(1H-1,2,4-triazole-1-yl)-spiro-[1,3-dioxolane-2,1'(2'H)-naphthalene. This compound had a melting point of 108° C.

후처리

  1. additionA mixture of 10 g
  2. customThe solvent was evaporated
  3. customleaving a slurry which
  4. washwashed twice with 10% aqueous sodium hydroxide and once with water
  5. dry with materialThe extract was dried in sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customleaving an oily residue which
  9. customcrystallized
  10. temperatureon cooling
  11. customto yield 1.5 g

출처 및 근거

ORD 기록
ord-48027628fa7447ea9860ebb15c41398f
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04943311

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