Cyclohexanecarboxylic acid → N-(5-Phenylthiophen-2-yl)cyclohexanecarboxamide

HRID 1448710Notes

Reaction equation

HRID 1448710 reaction equation
C([C:4]1[C:8](C)=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:6][C:5]=1[NH:16][C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18])(O)=O.[Li]I.O.O.C1(C(O)=O)CCCCC1>N1C(C)=CC(C)=CC=1C>[C:10]1([C:7]2[S:6][C:5]([NH:16][C:17]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[O:18])=[CH:4][CH:8]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7413Cyclohexanecarboxylic acidHCID 70592634N-(3-carboxy-methyl-5-phenyl-2-thienyl)-cyclohexane carboxamideHCID 178526965HCID 178526965, compound

Product 1

HCID 23341601N-(5-Phenylthiophen-2-yl)cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

This compound (m.p. 174° C.) was prepared from N-(3-carboxy-methyl-5-phenyl-2-thienyl)-cyclohexane carboxamide (31.1 g, 0.1 mole) and LiI.2H2O (48.1 g, 0.32 mole) by refluxing in collidine (125 ml.) according to the procedure of Example 53 (a). This compound was also prepared according to the procedure of Example 53(b), using cyclohexane carboxylic acid as the acylating agent. The products of the two processes were spectrally identical and had a melting point of 175° C.

Workup

  1. customThis compound was also prepared

Sources & evidence

ORD record
ord-7bedc89a3e994f288dc872cc93d3c31b
Source dataset
uspto-grants-1980_02
Patent number
US04187232

Reaction notes

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