HCID 178469794, compound → HCID 69419447, compound

HRID 916168Notes

Reaction equation

HRID 916168 reaction equation
[C:1]([NH:4][C:5]1S[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=[CH:19][C:7]=2[C:6]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])(=[O:3])[CH3:2]>[Ni]>[CH2:23]([O:22][C:20](=[O:21])[CH:6]([CH:7]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:8]1)[CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH3:24]

Participants

3

Reactant 1

HCID 178469794HCID 178469794, compound

Product 1

HCID 69419447HCID 69419447, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Ethyl 2-acetamidocyclododeca[b]thiophene-3-carboxylate (2.3366 g, 6.65 mmol) was reductively desulfurized using Raney nickel to yield the title compound as a yellow oil (2.1314 g, 6.55 mmol, 98.5%); TLC: Rf=0.75 (Solvent I), 0.46 (Solvent J); IR (cm−1). 3316 (NH), 2903 (CH aliphatic), 1725 (ester C═O), 1661 (amide C═O); 1H nmr (DMSO-d6): δ 7.88 (br s, 1H), 4.05 (q, 2H, J=8.1 Hz), 3.59 (m, 2H), 2.45 (m, 1H), 1.74 (s, 3H), 1.50 (m, 1H), 1.28 (m, 22H), 1.15 (t, 3H, J=8.1 Hz).

Sources & evidence

ORD record
ord-2bc97d9ebecb4f71bf4709d3fce2914b
Source dataset
uspto-grants-2007_09
Patent number
US07268164B2

Reaction notes

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