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

HRID 2082772

Reaktionsgleichung

Reaktionsgleichung von HRID 2082772
NC1SC(C2C=CC=CC=2)=CC=1C(OC)=O.C(CC(OC)=O)#N.C(Cl)(=O)C1C=CC=CC=1.[C:33]([CH2:36][C:37]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[S:39][C:38]=1[NH:48][C:49]([CH:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1)=[O:50])([OH:35])=[O:34]>CN(C)P(N(C)C)(N(C)C)=O.O>[C:33]([CH2:36][C:37]1[CH:41]=[C:40]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[S:39][C:38]=1[NH:48][C:49](=[O:50])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([OH:35])=[O:34]

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 7747Methyl cyanoacetateHCID 705256Methyl 2-amino-5-phenylthiophene-3-carboxylateHCID 23341632HCID 23341632, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 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. Similarly prepared was: N-(3-Carboxymethyl-5-phenyl-2-thienyl) cyclohexane carboxamide, m.p. 121°-122° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-47bb0a7efc064b86a30d65c93c0fa913
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04082771

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