Water → (2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetic acid

HRID 377390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377390
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)/[C:8]([OH:10])=[O:9])[N:6]=1.[Cl:32]N1C(=O)CCC1=O.O>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]([Cl:32])=[C:5](/[C:7](=[N:11]/[O:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)/[C:8]([OH:10])=[O:9])[N:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 10117176(Z)-2-(2-Aminothiazol-4-yl)-2-((trityloxy)imino)acetic acid

Produkt 1

HCID 10600185(2Z)-2-(2-amino-5-chloro-1,3-thiazol-4-yl)-2-trityloxyiminoacetic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)ace tic acid (5.81 g, 13.47 mmol) in DMF (30 mL) at room temperature (1 mL) was added N-chlorosuccinimide (1.80 g, 13.47 mmol). After overnight reaction the reaction mixture was poured into water (about 500 mL) and the resulting precipitate was filtered, washed with water and then with ethyl acetate and dried in vacuum to afford 4.43 g (71%) of the title compound. 13C NMR (CDCl3) δ108.5, 125.6, 126.2, 126.6, 12.3, 134.7 141.8, 146.5, 162.1, 163.3.

Aufarbeitung

  1. customAfter overnight reaction the reaction mixture
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water
  4. dry with materialwith ethyl acetate and dried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4478089c4fd54d709abd4a24e4dfac23
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025352

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