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

HRID 2082772

Reaction equation

HRID 2082772 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-47bb0a7efc064b86a30d65c93c0fa913
Source dataset
uspto-grants-1978_04
Patent number
US04082771

Linked notes

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