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

HRID 27664

Reaction equation

HRID 27664 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 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.

Workup

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

Sources & evidence

ORD record
ord-c2d28016781d4b6db6ad247f32ac93ef
Source dataset
uspto-grants-1980_09
Patent number
US04222946

Linked notes

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