Glyoxylic acid, monohydrate → Hwa 131

HRID 1165133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1165133
O.[C:2]([OH:6])(=O)[CH:3]=O.Br.[NH2:8][C:9]1[S:10][CH2:11][C:12]([C:15]2[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=2)=[N:13][N:14]=1>O.C(O)(=O)C.Cl>[C:26]([C:17]1[CH:16]=[C:15]([C:12]2[N:14]3[N:13]=[CH:3][C:2](=[O:6])[N:8]=[C:9]3[S:10][CH:11]=2)[CH:20]=[C:19]([C:21]([CH3:24])([CH3:22])[CH3:23])[C:18]=1[OH:25])([CH3:29])([CH3:27])[CH3:28]

Komponenten

6

Edukt 2

HCID 15620607Glyoxylic acid, monohydrateHCID 136364585HCID 136364585, Verbindung

Produkt 1

HCID 159492Hwa 131

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4.8 g (0.05 mol) of glyoxylic acid monohydrate in 75 ml of water were added dropwise to a solution of 10.0 g (0.025 mol) of 2-amino-5-(3,5-di-tert.butyl-4-hydroxyphenyl)-6H-1,3,4-thiadiazine hydrobromide from step (c1) in 250 ml of glacial acetic acid and 25 ml of 4N hydrochloric acid at 80° C. After the mixture had been stirred at 80° C. for 20 hours, it was evaporated under reduced pressure. It was advantageously possible to purify the solid residue by column chromatography on silica gel using methylene chloride/methanol (25:1) as the eluent and subsequent recrystallization from ethanol, and, from analytical and spectroscopic investigations, the product proved to be identical to that prepared by procedures (a) and (b).

Aufarbeitung

  1. customit was evaporated under reduced pressure
  2. customto purify the solid residue by column chromatography on silica gel
  3. customas the eluent and subsequent recrystallization from ethanol
  4. customthat prepared by procedures (a) and (b)

Quellen und Nachweise

ORD-Eintrag
ord-bddf200e56554c92af1d877521486423
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04908364

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