Sodium Hydroxide → 1-[4-(Cyano-methylamino-methyl)-thiazol-2-yl]-3-(3-fluoro-benzyl)-urea
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15]O)[N:14]=1)=[O:8].[NH2:20][C:21]1SC=C(COC(=O)C)N=1.FC1C=C(C=CC=1)[CH2:35][N:36]=C=O.[OH-].[Na+]>C1COCC1.CCOC(C)=O.CO>[C:21]([CH:15]([NH:36][CH3:35])[C:13]1[N:14]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]2[CH:17]=[CH:18][CH:19]=[C:2]([F:1])[CH:3]=2)=[O:8])[S:11][CH:12]=1)#[N:20]Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
Preparation of -(3-fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea. To a solution of acetic acid 2-amino-thiazol-4-ylmethyl ester (6.89 g) in THF (50 mL) were 3-fluorobenzylisocyanate (5.50 g) and TEA (5.03 mL) added. The resultant solution was heated at 70° C. over 2 h. Then, MeOH (30 mL) and NaOH (6N, 15 mL) were added to the above solution. The reaction mixture was heated at 60° C. for 30 min After cooling down, the reaction mixture was diluted with EtOAc (150 mL) and was washed with water. The organic solvents were concentrated and the residue was purified by silica-gel column chromatography to afford 8.29 g of the desired product-1-(3-fluoro-benzyl)-3-(4-hydroxymethyl-thiazol-2-yl)-urea.
Aufarbeitung
- additionadded
- temperatureAfter cooling down
- washwas washed with water
- concentrationThe organic solvents were concentrated
- customthe residue was purified by silica-gel column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-0ca05ccaa8d84add919c842cf41e17a6
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08148380B2
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