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Hydrochloric Acid → Acetic acid, oxo((4-phenyl-2-thiazolyl)amino)-, 2-methoxyethyl ester

HRID 647122
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 647122
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13](=[O:17])[C:14]([OH:16])=[O:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O-:21])(=O)[CH3:19].[K+].Cl.[C:24](Cl)(=O)C(Cl)=O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13](=[O:17])[C:14]([O:16][CH2:19][CH2:18][O:21][CH3:24])=[O:15])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 517044Potassium AcetateHCID 4713520N-(4-phenyl-thiazol-2-yl)-oxamic acid

Produkt 1

HCID 3067448Acetic acid, oxo((4-phenyl-2-thiazolyl)amino)-, 2-methoxyethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

6.2 g of N-(4-phenyl-thiazol-2-yl)-oxamic acid (prepared from the ethyl ester by hydrolyzing with aqueous potassium acetate and liberating the acid with dilute hydrochloric acid), in 25 ml of dry toluene, are heated with 20 ml of oxalyl chloride for 2 hours at 60° C. After distilling off the excess oxalyl chloride under reduced pressure, a solution of 5 ml of ethylene glycol monomethyl ether, 3.5 ml of triethylamine and 20 ml of toluene is added dropwise. The mixture is stirred for a further 3 hours at room temperature and is then left to stand overnight. The precipitate is filtered off, washed with methanol and water and recrystallized from ethanol. 3.7 g of the compound of the formula I, with R1 =C6H5 and R2 =CH2CH2OCH3, of melting point 118°-120° C., are obtained.

Aufarbeitung

  1. distillationAfter distilling off the excess oxalyl chloride under reduced pressure
  2. additiona solution of 5 ml of ethylene glycol monomethyl ether, 3.5 ml of triethylamine and 20 ml of toluene is added dropwise
  3. waitis then left
  4. waitto stand overnight
  5. filtrationThe precipitate is filtered off
  6. washwashed with methanol and water
  7. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f8d2c993b5244a7a85cf80b523e41f0f
Quelldatensatz
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04407810

Notizen zur Reaktion

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