Triethylamine → Proquinazid

HRID 1276613

Reaktionsgleichung

Reaktionsgleichung von HRID 1276613
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.[CH2:19]([N:22]=[C:23](SC)[O:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH3:21]>C(O)CC>[I:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[N:1]=[C:23]([O:24][CH2:25][CH2:26][CH3:27])[N:22]([CH2:19][CH2:20][CH3:21])[C:4]2=[O:6]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 22116536HCID 22116536, Verbindung

Produkt 1

HCID 11057771ProquinazidAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

To a solution of 0.38 g (1.44 mmoles) of 2-amino-5-iodobenzoic acid and 0.14 g (1.38 mmol) of triethylamine in 7.15 mL of n-propanol was added 0.25 g (1.143 mmol) of S-methyl O-propyl propylcarbonimidothioate. The reaction mixture was stirred at room temperature for 18 h, heated to 60° C. for 24 h, and then heated to reflux for 6 h. The reaction was then concentrated under reduced pressure to give about 0.6 g of crude material, which was purified by flash chromatography on silica (93:7 hexanes:ethyl acetate) to give 0.21 g of the title compound, 1H NMR (400 MHz, CDCl3): δ0.96 (t,3H); 1.06 (t,3H); 1.64-1.79 (m,2H); 1.81-1.92 (m,2H); 4.05 (t,2H); 4.43 (t,2H), 7.19 (d,1H); 7.85 (dd,1H); 8.49 (d,1H). In addition, 0.11 g of propyl-5-iodoanthranilate was obtained from the flash chromatography, 1H NMR (400 MHz, CDCl3): δ1.02 (t,3H); 1.76-1.86 (m,2H); 4.23 (t,2H); 5.8 (br s,2H); 6.45 (d,1H); 7.45 (dd, 1H); 8.13 (d,1H).

Aufarbeitung

  1. temperatureheated to 60° C. for 24 h
  2. temperatureheated
  3. temperatureto reflux for 6 h
  4. concentrationThe reaction was then concentrated under reduced pressure
  5. customto give about 0.6 g of crude material, which
  6. customwas purified by flash chromatography on silica (93:7 hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ca151025250e46d5b77fd42bb79c9ebe
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166208

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