Benzoyl isothiocyanate → N-{4-[2-(4-{[(benzoylamino)carbonothioyl]amino)phenyl)ethyl]-1,3-thiazol-2-yl}acetamide

HRID 1246429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1246429
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1.[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[C:19]([NH:27][C:28]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:4][CH:3]=1)=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 68284Benzoyl isothiocyanateHCID 21914814N-{4-[2-(4-aminophenyl)ethyl]thiazol-2-yl}acetamide

Produkt 1

HCID 21914854N-{4-[2-(4-{[(benzoylamino)carbonothioyl]amino)phenyl)ethyl]-1,3-thiazol-2-yl}acetamideAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cold solution of N-(4-(2-(4-aminophenyl)ethyl)-1,3-thiazol-2-yl)acetamide (300 mg) prepared in a similar manner according to Step 6 of Production Example 1 in acetone (5 ml) was added benzoyl isothiocyanate (187 mg) and the mixture was refluxed for 2 hours. The reaction mixture was cooled to 0° C. The precipitated crystals were filtered and washed with ice-cold acetone to give N-{4-[2-(4-{[(benzoylamino)carbonothioyl]amino}phenyl)ethyl]-1,3-thiazol-2-yl}acetamide (359 mg).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. filtrationThe precipitated crystals were filtered
  3. washwashed with ice-cold acetone

Quellen und Nachweise

ORD-Eintrag
ord-49db6f5c0f844f14bc524438b8c54906
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125901B2

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