Potassium Carbonate → HCID 140357400, Verbindung

HRID 2249152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2249152
Cl.[OH:2]/[N:3]=[C:4](/[C:10]1[N:11]=[C:12]([NH:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:13][CH:14]=1)\[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:42][F:43]>CS(C)=O.C(Cl)Cl>[F:43][CH2:42][O:2]/[N:3]=[C:4](/[C:10]1[N:11]=[C:12]([NH:15][C:16]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:13][CH:14]=1)\[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 61108BromofluoromethaneHCID 9589415(Z)-Ethyl 2-(hydroxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetate hydrochloride

Produkt 1

HCID 140357400HCID 140357400, VerbindungAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl (Z)-2-hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)acetate, hydrochloride salt (8.7 g) was stirred with potassium carbonate (15.35 g) in dimethyl sulphoxide (30 ml) under nitrogen at 21° . Bromofluoromethane (ca 3 g) was added. The nitrogen flow was stopped and the stirring continued for two hours. The mixture was poured into an ice-water mixture with stirring and the solid was collected by filtration and washed with water. The solid was dissolved in methylene chloride and the organic layer was separated and dried with magnesium sulphate. Evaporation gave a foam. This was dissolved in methylene chloride and pre-absorbed onto Kieselgel 60 (50 g). This was added to the top of a column of similar silica (125 g) set up in 10% ethyl acetate in cyclohexane. The column was eluted successively with 10%, 20% and 33% ethyl acetate in cyclohexane. After combination of appropriate fractions, evaporation gave the title compound (8.06 g) as a foam; λmax (EtOH) 302 nm (E1 cm1% 92), λinfl include 227.5 nm (E1 cm1% 546) and 259 nm (E1 cm1% 221), νmax (CHBr3) 3400 (NH), 1739 (ester) and 1533 cm-1 (C=N).

Aufarbeitung

  1. filtrationthe solid was collected by filtration
  2. washwashed with water
  3. dissolutionThe solid was dissolved in methylene chloride
  4. customthe organic layer was separated
  5. dry with materialdried with magnesium sulphate
  6. customEvaporation
  7. customgave a foam
  8. custompre-absorbed onto Kieselgel 60 (50 g)
  9. additionThis was added to the top of a column of similar silica (125 g)
  10. washThe column was eluted successively with 10%, 20% and 33% ethyl acetate in cyclohexane
  11. customAfter combination of appropriate fractions, evaporation

Quellen und Nachweise

ORD-Eintrag
ord-c80679db3f604e4fae0a06611f7fc0dd
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05043334

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