4-Chlorobenzoyl chloride → 4-[p-chloro-N-(6-methoxybiphenyl-3-yl)-benzamido]butyric acid
Reaktionsgleichung
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([NH:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1.[OH-].[K+]>C1C=CC=CC=1.C(O)C>[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([N:15]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:6]2[CH:7]=[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:39])=[CH:36][CH:35]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
8.0 g of ethyl 4-(6-methoxybiphenyl-3-yl)aminobutyrate and, 3.3 g of ethyldiisopropylamine in 50 ml of benzene are reacted, analogously to Example 47b), with 4.6 g of p-chlorobenzoyl chloride. The reaction product is dissolved in 50 ml of benzene and, after the addition thereto of a solution of 2.3 g of potassium hydroxide in 20 ml of ethanol, is then stirred for 8 hours at room temperature. After distilling off the solvent, the residue is dissolved in water; the resulting solution is acidified with dilute hydrochloric acid and extracted with diethyl ether. The residue (remaining after evaporating off the ether) is recrystallized from ethyl acetate/petrol ether (1:1) to obtain 8.1 g (73.5% of theory) of 4-[p-chloro-N-(6-methoxybiphenyl-3-yl)-benzamido]butyric acid, MP 114° to 116°.
Aufarbeitung
- additionafter the addition
- distillationAfter distilling off the solvent
- dissolutionthe residue is dissolved in water
- extractionextracted with diethyl ether
- customafter evaporating off the ether)
- customis recrystallized from ethyl acetate/petrol ether (1:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-0a6bdbb4d5554476bd64ffff8e6ae889
- Quelldatensatz
- uspto-grants-1981_01
- Patentnummer
- US04243678
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