Acetamide → 3,5-Dihydroxy-4-phenylazo-benzoic acid methyl ester

HRID 542946

Reaktionsgleichung

Reaktionsgleichung von HRID 542946
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][C:9](=[O:11])[C:8]([N:12]=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([OH:20])[CH2:6]1)=[O:4].C(N)(=O)C.BrC1CC(=O)NC1=O.BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[C:9]([OH:11])[C:8]([N:12]=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:7]([OH:20])[CH:6]=1

Komponenten

6

Edukt 4

HCID 178AcetamideHCID 24408BromineHCID 38309BromosuccinimideHCID 1360563743-Hydroxy-5-keto-4-phenylazo-3-cyclohexenecarboxylic acid methyl ester

Produkt 1

HCID 1360597863,5-Dihydroxy-4-phenylazo-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

54.8 G. of 3-hydroxy-5-keto-4-phenylazo-3-cyclohexene-carboxylic acid methyl ester, 12.0 g. of acetamide and 2.0 g. of bromosuccinimide were stirred in 600 ml. of chloroform and treated dropwise with 32.0 g. of bromine in 400 ml. of chloroform (the reaction temperature being held below 35° C.). Soon, the separation of acetamide hydrobromide began. The mixture was stirred for an additional 30 minutes at room temperature. Then, the acetamide hydrobromide was removed by filtration and the filtrate evaporated to dryness. The residue was taken up in a small amount of ethanol, filtered under vacuum and washed with ethanol, whereby there was obtained 3,5-dihydroxy-4-phenylazo-benzoic acid methyl ester having a melting point of 216°-218° C.

Aufarbeitung

  1. custombeing held below 35° C.
  2. customSoon, the separation of acetamide hydrobromide
  3. customThen, the acetamide hydrobromide was removed by filtration
  4. customthe filtrate evaporated to dryness
  5. filtrationfiltered under vacuum
  6. washwashed with ethanol

Quellen und Nachweise

ORD-Eintrag
ord-c618d38ee934436caf75044392b6e4b7
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659818

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