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Water → HCID 13338941, Verbindung

HRID 978896
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 978896
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1.C(N(CC)CC)C.[C:21](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O>[C:21]([NH:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[OH:13])/[C:8]([O:10][CH3:11])=[O:9])[N:6]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 6411353Methyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Produkt 1

HCID 13338941HCID 13338941, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

In 10 ml of N,N-dimethylformamide is dissolved 4.62 g of methyl 2-(2-amino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate, followed by addition of 3 ml of triethylamine. Then, under stirring at -30° C., 6.42 g of trityl chloride is added over one hour. The mixture is further stirred at that temperature for one hour and, then at 15° C. for an additional 2 hours. To this reaction mixture is added 200 ml of water, followed by extraction with 200 ml of ethyl acetate. The ethyl acetate extract is washed twice with 200 ml portions of water and dried over anhydrous sodium sulfate. The solvent is then distilled off. The residue is purified by column chromatography [silica gel: 100 g; eluent:hexane-ethyl acetate (1:1)] and the resultant crystals are recrystallized from ethyl acetate to give methyl 2-(2-tritylamino-4-thiazolyl)-(Z)-2-hydroxyiminoacetate as colorless granules, m.p. 294°-205° C.

Aufarbeitung

  1. stirringThe mixture is further stirred at that temperature for one hour
  2. extractionfollowed by extraction with 200 ml of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed twice with 200 ml portions of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off
  7. customThe residue is purified by column chromatography [silica gel: 100 g; eluent:hexane-ethyl acetate (1:1)]
  8. customthe resultant crystals are recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-db0fff7e9070492b854107c4a4ba4eda
Quelldatensatz
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04665067

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