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N-[3-(acetyl-methyl-amino)-5-amino-phenyl]-N-methyl-acetamide → HCID 19353552, Verbindung

HRID 1584211
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1584211
[C:1]([N:4]([CH3:17])[C:5]1[CH:6]=[C:7]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[CH:8]=[C:9]([NH2:11])[CH:10]=1)(=[O:3])[CH3:2].[NH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19]([CH3:21])=[O:20].[S:28](Cl)(O)(=[O:30])=[O:29]>N1C=CC=CC=1.O>[C:19]([NH:18][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:11][C:9]2[CH:8]=[C:7]([N:12]([CH3:16])[C:13](=[O:15])[CH3:14])[CH:6]=[C:5]([N:4]([C:1](=[O:3])[CH3:2])[CH3:17])[CH:10]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1)(=[O:20])[CH3:21]
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Komponenten

5

Edukt 2

HCID 10776126N-[3-(acetyl-methyl-amino)-5-amino-phenyl]-N-methyl-acetamideHCID 19353479HCID 19353479, Verbindung

Produkt 1

HCID 19353552HCID 19353552, VerbindungAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

0.15 g (0.00063 mol) of N-[3-(acetyl-methyl-amino)-5-amino-phenyl]-N-methyl-acetamide was dissolved in 3 ml of pyridine, treated with 0.154 g (0.00064 mol) of 4-acetamino-benzene-sulfochloride and stirred at room temperature for 16 hours. Subsequently, the mixture was freed from solvent, the residue was taken up in 25 ml of water, extracted four times with 200 ml of ethyl acetate each time and the combined organic phases were washed with saturated sodium chloride solution and dried over sodium sulfate. After removal of the solvent the residue was chromatographed on silica gel, firstly with 2% and then 5% methanol in dichloromethane. There was obtained 0.15 g (55%) of N-[3-(4-acetylamino-phenylsulfonylamino)-5-(acetyl-methyl-amino)-phenyl]-N-methyl-acetamide as an orange colored, amorphous solid. MS (ISN): me/e=431 (C20H23N4O5S-).

Aufarbeitung

  1. extractionextracted four times with 200 ml of ethyl acetate each time
  2. washthe combined organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent the residue
  5. customwas chromatographed on silica gel, firstly with 2%

Quellen und Nachweise

ORD-Eintrag
ord-0f71de3ff2b04fa3aa176113456c86e0
Quelldatensatz
uspto-grants-1999_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05932599

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