Triethylamine → 1-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-one

HRID 343616

Reaktionsgleichung

Reaktionsgleichung von HRID 343616
[CH2:1]([NH:8][CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[S:25])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:9][C:10](=[O:12])[N:23]([C:20]2[CH:21]=[CH:22][C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][CH:19]=2)[C:24]1=[S:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 869652-(Benzylamino)acetic acidHCID 1410041-Butyl-4-isothiocyanatobenzene

Produkt 1

HCID 857014301-Benzyl-3-(4-butylphenyl)-2-thioxo-imidazolidin-4-oneAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of N-benzyl glycine (8.7 g), 4-n-butylphenyl-isothiocyanate (8.55 g), triethyl amine (5.5 g) and chloroform (150 mL) was heated at reflux for 5 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (400 mL) and water (2×300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness. Crystallization from ethyl acetate afforded the title compound (11.4 g) as an off-white solid, m.p. 149°-151° C. Anal. Calcd. for. C20H22N2OS: C, 70.97; H, 6.55; N, 8.28. Found: C, 70.81; H, 6.76; N, 8.32. Mass spectrum (EI, M.+) m/z 338.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate (400 mL)
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customCrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-46d51c1801f24acca3a1477cfdc58d95
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861517

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