2-Benzoylbenzoic Acid → 3-(2-Benzoylbenzoyl)-4-thiazolidinemethanol

HRID 1457326

Reaktionsgleichung

Reaktionsgleichung von HRID 1457326
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[S:29]1[CH2:33][CH:32]([CH2:34][OH:35])[NH:31][CH2:30]1.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([N:31]1[CH:32]([CH2:34][OH:35])[CH2:33][S:29][CH2:30]1)=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 68132-Benzoylbenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3213334-ThiazolidinemethanolHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 221044663-(2-Benzoylbenzoyl)-4-thiazolidinemethanolAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.9 g (8.4 mmol) of o-benzoylbenzoic acid and 1.13 g (8.4 mmol) of 1-hydroxybenzotriazole hydrate were combined in 50 ml of methylene chloride and stirred for 20 minutes at room temperature. 1.0 g (8.4 mmol) of 4-thiazolidinemethanol was added, followed by 1.6 g (8.4 mmol) of ethyl-3-(3-dimethylaminopropyl)carbodiimide. The reaction mixture was stirred for 18 hours at room temperature and washed with water, first at pH 2.5 and then at pH 9.5. The organic phase was dried and evaporated to give a foam which was chromatographed on silica gel using 1:1/chloroform:ethyl acetate as the eluant to yield 1.1 g (40%) of the title compound. 1H NMR (CDCl3) δ: 7.4-7.85(m,9H); 4.65(m,1H) ; 4.20-4.40(m,2H); 3.96(m,1H); 3.60-3.70(m,2H); 3.0-3.30(m,2H). High Resolution Mass Spectrum: m/e=328.1015±0.8 ppm (calculated for C18H18NO3S).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 18 hours at room temperature
  2. washwashed with water, first at pH 2.5
  3. customThe organic phase was dried
  4. customevaporated
  5. customto give a foam which
  6. customwas chromatographed on silica gel using 1:1/chloroform

Quellen und Nachweise

ORD-Eintrag
ord-21cea4eb360c472eb84462b7a0d7079c
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05847155

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