HCID 22339842, compound → HCID 69417812, compound

HRID 916171Notes

Reaction equation

HRID 916171 reaction equation
[C:1]([NH:4][C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)S[C:6]=1[C:17]([O:19][CH3:20])=[O:18])(=[O:3])[CH3:2]>[Ni]>[CH3:20][O:19][C:17](=[O:18])[CH2:6][CH:5]([CH2:9][CH2:8][C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 22339842HCID 22339842, compound

Product 1

HCID 69417812HCID 69417812, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Methyl 3-acetamido-5-(4-methylphenyl)thiophene-2-carboxylate (1.4905 g, 5.15 mmol) was reductively desulfurized using Raney nickel to yield the title compound as a white gum (1.3434 g, 5.10 mmol, 99.1%); mp: 50-51° C.; TLC: Rf=0.63 (Solvent I), 0.85 (Solvent L); IR (cm1): 3288 (NH), 2906 (CH aliphatic), 1731 (ester C═O), 1639 (amide C═O), 807 (═CH); 1H nmr (CDCl3): δ 7.07 (s, 4H), 6.08 (br d, 1H, J=8.8 Hz), 4.28 (sextet, 1H, J=5.3 Hz), 3.67 (s, 3H), 2.63 (d, 2H, J=8.2 Hz), 2.55 (m, 2H), 2.30 (s, 3H), 1.96 (s, 3H), 1.84 (quintet, 2H, J=7.9 Hz).

Sources & evidence

ORD record
ord-fc114fac996146ceabb1b325b163d8d9
Source dataset
uspto-grants-2007_09
Patent number
US07268164B2

Reaction notes

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