Butylurea → N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl-urea

HRID 894095

Reaktionsgleichung

Reaktionsgleichung von HRID 894095
[CH2:1]([NH:5][C:6]([NH2:8])=[O:7])[CH2:2][CH2:3][CH3:4].[H-].[Na+].[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:21]([NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:22].[S:32](Cl)(O)(=[O:34])=[O:33]>O1CCCC1>[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][N:13]1[C:21]([NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:8][C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])(=[O:34])=[O:33])=[CH:28][CH:27]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 11595ButylureaHCID 24758Sodium hydrideHCID 211623494-[2-(1-Oxo-isoindoline-2-carboxamido)-ethyl]-benzene sulfochloride

Produkt 1

HCID 21162325N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzenesulfonyl)-N'-butyl-urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

4.8 g of butyl urea are dissolved in 100 ml of tetrahydrofurane and, while stirring, 1.5 g of 80% sodium hydride (in oil) are added. The mixture is heated for 3 hours to 60° C. whereupon 7.6 g of 4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]-benzene-sulfochloride in 100 ml of tetrahydrofurane are added while cooling. The temperature is slowly raised to 60°-70° C. and stirring is continued at that temperature for 3 hours. The solvent is removed under reduced pressure, water is added to the residue, the mixture is filtered and the filtrate is acidified with dilute hydrochloric acid. After recrystallization from dilute acetone, the N-(4-[2-(1-oxo-isoindoline-2-carboxamido)-ethyl]benzenesulfonyl)-N'-butyl-urea melts at 189°-190° C.

Aufarbeitung

  1. additionare added
  2. temperaturewhile cooling
  3. temperatureThe temperature is slowly raised to 60°-70° C.
  4. stirringstirring
  5. customThe solvent is removed under reduced pressure, water
  6. additionis added to the residue
  7. filtrationthe mixture is filtered
  8. customAfter recrystallization from dilute acetone

Quellen und Nachweise

ORD-Eintrag
ord-eeaef196eedc4b268efebd985dfcd232
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04282239

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