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

HRID 2082774Notes

Reaction equation

HRID 2082774 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-].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 66321Lithium iodideHCID 70592634N-(3-carboxy-methyl-5-phenyl-2-thienyl)-cyclohexane carboxamide

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-e7338ab3358949d39b2f0d953f797e84
Source dataset
uspto-grants-1978_04
Patent number
US04082771

Reaction notes

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