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

HRID 342937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342937
[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)acetic acid (5.81 g, 13.47 mmol) in DMF (30 mL) at room temperature (lmL) 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) δ 108.5, 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-5b9b5ed4b24243209d193d58ff6a4f2e
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859256

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