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Hydrochloric Acid → Methyl 4-iodo-2-[N-(N-butylaminocarbonyl)aminosulfonyl]benzoate

HRID 1857825
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1857825
[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:22]([N:26]=[C:27]=[O:28])[CH2:23][CH2:24][CH3:25].Cl>ClC1C=CC=CC=1.O>[I:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([S:12]([NH:15][C:27]([NH:26][CH2:22][CH2:23][CH2:24][CH3:25])=[O:28])(=[O:13])=[O:14])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 109478222-(Aminosulfonyl)-4-iodobenzoic acid methyl ester

Produkt 1

HCID 10863097Methyl 4-iodo-2-[N-(N-butylaminocarbonyl)aminosulfonyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

34.1 g (0.1 mol) of the sulfonamide of the formula (IV) from Example 1 and 14.7 g of K2CO3 (0.105 mol) are admixed with 10.6 g of n-butyl isocyanate (98% pure) (0.105 mol) in 250 ml of chlorobenzene, and the mixture is kept at 55 to 60° C. for 2 hours. The mixture is then stirred at 90° C. for 8.5 h. The mixture is cooled to room temperature and initially 200 ml of water and then 2n of hydrochloric acid are added until the pH has reached 1-2. The organic phase is separated off and washed free of acid using four times 50 ml of water. The solvent is removed under reduced pressure, and 43.8 g of the desired compound of the formula (I) (99.3% of theory) of melting point 128 to 130° C. remain.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. customThe organic phase is separated off
  3. washwashed free of acid
  4. customThe solvent is removed under reduced pressure, and 43.8 g of the desired compound of the formula (I) (99.3% of theory) of melting point 128 to 130° C.

Quellen und Nachweise

ORD-Eintrag
ord-64742d227bd8490ca2adb61bff4c49e2
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06147248

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