N'-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine → Ethanone, 1-(2-chlorophenyl)-

HRID 401589

Reaktionsgleichung

Reaktionsgleichung von HRID 401589
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([C:6]1[S:10][C:9]([N:11]=CN(C)C)=[N:8][CH:7]=1)=[O:5]>Cl>[NH2:11][C:9]1[S:10][C:6]([C:4]([C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=2[Cl:1])=[O:5])=[CH:7][N:8]=1.[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4](=[O:5])[CH3:6]

Komponenten

4

Edukt 1

HCID 66628633N'-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine

Produkt 2

HCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 574569435-[(2-Chlorophenyl)carbonyl]-1,3-thiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The crude N′-[5-(2-chloro-benzoyl)-thiazol-2-yl]-N,N-dimethyl-formamidine was dissolved in 10% aqueous hydrochloric acid (150 mL) and heated to 70° C. for 4 hours. The precipitate was filtered, washed with ether, and then suspended in a 10% aqueous sodium carbonate solution (250 mL). The suspension was stirred for 1 hour and the precipitate was filtered, washed with ether, and dried in air to give (2-amino-thiazol-5-yl)-(2-chloro-phenyl)-methanone as a brown solid (8.5 g, 36 mmol, 55% from 1-(2-chloro-phenyl)-ethanone). ESI-MS m/z calc. 238.0. found 239.3 (M+1)+ 1H NMR (DMSO): δ: 7.252 (s, 1H), 7.420-7.553 (m, 4H), 8.345 (s, 2H).

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. washwashed with ether
  3. filtrationthe precipitate was filtered
  4. washwashed with ether
  5. customdried in air

Quellen und Nachweise

ORD-Eintrag
ord-45d7da0e73ac49708d4b0486ffecee4f
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741939B2

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