Potassium Iodide → 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

HRID 1914613

Reaktionsgleichung

Reaktionsgleichung von HRID 1914613
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Cl[CH2:14][C:15]1[N:16]=[C:17]([NH2:20])[S:18][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C.O>[NH2:20][C:17]1[S:18][CH:19]=[C:15]([CH2:14][O:1][N:2]2[C:3](=[O:12])[C:4]3[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=[O:7])[N:16]=1

Komponenten

7

Edukt 4

HCID 4875Potassium IodideHCID 10665N-HydroxyphthalimideHCID 10796Cesium carbonateHCID 732294-Chloromethylthiazol-2-ylamine

Produkt 1

HCID 3410772-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of N-hydroxyphthalimide (50.0 g, 306 mmol), 4-(chloromethyl)-1,3-thiazol-2-amine (50.1 g, 337 mmol), cesium carbonate (210 g, 0.64 mol) and potassium iodide (2.54 g, 15.3 mmol) in acetonitrile (440 mL) was stirred at room temperature for 18 h. Water (300 mL) was added, the precipitate was filtered off and washed with water until colourless, then dried in vacuo overnight to afford 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione as a colourless solid [36.0 g; 43% of theory; HPLC/MS: m/z=276 (M+H); log P(HCOOH)=0.74].

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. washwashed with water until colourless,
  3. customthen dried in vacuo overnight

Quellen und Nachweise

ORD-Eintrag
ord-386cc9bab711421ead518e0e0c58ee48
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614217B2

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