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Dimethylformamide → HCID 14230767, Verbindung

HRID 465256
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 465256
CN(C)C=O.[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:36]/[OH:37])/[C:32]([O:34][CH3:35])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:44](Br)[CH:45]=[CH2:46]>O>[C:6]([NH:25][C:26]1[S:27][CH:28]=[C:29](/[C:31](=[N:36]/[O:37][CH2:46][CH:45]=[CH2:44])/[C:32]([O:34][CH3:35])=[O:33])[N:30]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7841Allyl bromide2×HCID 11430Potassium Carbonate2×HCID 13338941HCID 13338941, Verbindung

Produkt 1

HCID 14230767HCID 14230767, VerbindungAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To 70.5 ml of N,N-dimethylformamide are added 7.05 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate and 3.3 g of potassium carbonate. Then, under ice-cooling and stirring 2.12 g of allyl bromide is added dropwise over a period of 5 minutes. The mixture is further stirred under ice-cooling for 4 hours. To this reaction mixture are added 1.65 g of potassium carbonate and 1.06 g of allyl bromide, and the mixture is stirred for an additional 4 hours. The reaction mixture is diluted with 150 ml of water and extracted three times with 100 ml portions of ether. The ether extract is washed twice with 100 ml portios of aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is purified by column chromatography [silica gel: 300 g; eluent: hexane-ethyl acetate (1:1)] and crystallized from ether-hexane to give 7.0 g of methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-allyloxyiminoacetate, m.p. 115°- 116° C.

Aufarbeitung

  1. temperatureThen, under ice-cooling
  2. additionis added dropwise over a period of 5 minutes
  3. temperaturecooling for 4 hours
  4. stirringthe mixture is stirred for an additional 4 hours
  5. extractionextracted three times with 100 ml portions of ether
  6. extractionThe ether extract
  7. washis washed twice with 100 ml portios of aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off
  10. customthe residue is purified by column chromatography [silica gel: 300 g; eluent: hexane-ethyl acetate (1:1)]
  11. customcrystallized from ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-40a7d6439fa34709be6807058cb7662d
Quelldatensatz
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04550105

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