Sulfamethazine → HCID 23504900, Verbindung

HRID 1884823

Reaktionsgleichung

Reaktionsgleichung von HRID 1884823
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH3:31])[N:17]=[C:18]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[N:19]=1.C(N(CC)CC)C.C(N=C=NC(C)C)(C)C>C(Cl)(Cl)Cl>[CH3:31][C:16]1[CH:15]=[C:14]([CH3:13])[N:19]=[C:18]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:10](=[O:12])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[N:17]=1

Komponenten

6

Edukt 4

HCID 5327SulfamethazineHCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 12734Diisopropylcarbodiimide

Produkt 1

HCID 23504900HCID 23504900, VerbindungAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Methoxyphenylacetic acid (33 mg, 0.20 mmol) and sulfamethazine (55 mg, 0.20 mmol) were dissolved in 4 ml of chloroform. Triethylamine (70 μl, 0.55 mmol) and diisopropylcarbodiimide (50 μl, 0.20 mmol) were added to the reaction mixture. Solution was stirred and refluxed overnight. The reaction mixture was then evaporated to dryness, washed with water and purified on silica using gradient elution (chloroform to 2% methanol in chloroform) to obtain white crystals with the yield of 40%. 1H NMR (CDCl3, 500 MHz): 8.04 (2H, m), 7.54 (2H, m), 7.30 (2H, m), 6.98 (2H, m), 6.60 (1H, s), 3.95 (3H, s), 3.72 (2H, s), 2.33 (6H, s); MS (ESI+): m/z 449 (M+Na)+, 427 (M+H)+.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. washwashed with water
  4. custompurified on silica using gradient elution (chloroform to 2% methanol in chloroform)
  5. customto obtain white crystals with the yield of 40%

Quellen und Nachweise

ORD-Eintrag
ord-433da962c43a4fbf8a0b104ef2722b91
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06767909B2

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