Water → N-(3-Carboxymethyl-5-phenyl-2-thienyl)-benzamide

HRID 27664

Reaktionsgleichung

Reaktionsgleichung von HRID 27664
[NH2:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7](OC)=O.C(C[C:20]([O:22]C)=[O:21])#N.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)P(N(C)C)(N(C)C)=O>[C:20]([CH2:7][C:6]1[CH:5]=[C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:3][C:2]=1[NH:1][C:24](=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([OH:22])=[O:21]

Komponenten

6

Edukt 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 7747Methyl cyanoacetateHCID 705256Methyl 2-amino-5-phenylthiophene-3-carboxylate

Produkt 1

HCID 23341625N-(3-Carboxymethyl-5-phenyl-2-thienyl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

Methyl 2-amino-5-phenyl-thiophene-3-carboxylate (1.3 g, 0.0055 mole) in hexamethyl phosphoramide (prepared by the method of Chemische Berichte, 99, 94 (1966) but using methyl cyanoacetate in place of ethyl cyanoacetate) (20 ml.) was stirred and treated with benzoyl chloride (1.56 g, 1.28 ml, 0.011 mole). The solution was stirred for 2 hours, poured into water (750 ml), stored overnight and the title compound filtered off (1.31 g) m.p. 190° C.

Aufarbeitung

  1. stirringThe solution was stirred for 2 hours
  2. filtrationthe title compound filtered off (1.31 g) m.p. 190° C.

Quellen und Nachweise

ORD-Eintrag
ord-c2d28016781d4b6db6ad247f32ac93ef
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04222946

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