p-Toluenesulfonic acid → 6-Fluoro-2,3-dihydro-2',5'-dioxo-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2-carboxylic acid 3,6,9,12-tetraoxatridecyl ester

HRID 649533

Reaktionsgleichung

Reaktionsgleichung von HRID 649533
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:17][CH:16]([C:18]([OH:20])=[O:19])[CH2:15][C:8]3([C:12](=[O:13])[NH:11][C:10](=[O:14])[NH:9]3)[C:6]=2[CH:7]=1.[CH2:21](O)[CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:21]([O:19][C:18]([CH:16]1[CH2:15][C:8]2([C:12](=[O:13])[NH:11][C:10](=[O:14])[NH:9]2)[C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:17]1)=[O:20])[CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 90263Tetraethylene glycol monomethyl etherHCID 139359916-fluoro-2,3-dihydro-2',5'-dioxo-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2-carboxylic acid

Produkt 1

HCID 541376966-Fluoro-2,3-dihydro-2',5'-dioxo-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2-carboxylic acid 3,6,9,12-tetraoxatridecyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture consisting of 6-fluoro-2,3-dihydro-2',5'-dioxo-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2-carboxylic acid (2.8 g, 0.01 mol) (obtained through the process as described in Example 1), 3,6,9,12-tetraoxatridecanol (2.1 g, 0.01 mol) and p-toluenesulfonic acid (1.9 g, 0.01 mol) in 80 ml of toluene was heated at reflux temperature for 7.0 hours under a Dean-Stark trap. The reaction mixture was evaporated in vacuo to give a semi-solid residue which was partitioned between 50 ml of chloroform and 50 ml of water. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to give a pale yellow oil which was chromatographed on silica gel, eluting with ethyl acetate to give 3.9 g (82.5%) of the desired refined compound as a colorless oil.

Aufarbeitung

  1. customobtained through the process
  2. temperaturewas heated
  3. temperatureat reflux temperature for 7.0 hours under a Dean-Stark trap
  4. customThe reaction mixture was evaporated in vacuo
  5. customto give a semi-solid residue which
  6. customwas partitioned between 50 ml of chloroform and 50 ml of water
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto give a pale yellow oil which
  11. customwas chromatographed on silica gel
  12. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-77d69230e80e423a957f0968193c264e
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04740517

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