Lawesson's reagent → 1-Phenyltriazolylmethyl-3-methoxypyridine-2-thione

HRID 539527

Reaction equation

HRID 539527 reaction equation
[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[N:15]=[N:16][NH:17][CH:18]=3)=[C:9]([O:19][CH3:20])[C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]3[N:15]=[N:16][NH:17][CH:18]=3)=[C:9]([O:19][CH3:20])[C:8]2=[S:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 1784876421-Phenyltriazolylmethyl-3-methoxypyridine-2-one

Product 1

HCID 1784876431-Phenyltriazolylmethyl-3-methoxypyridine-2-thioneYield 156.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reaction of 151a (0.295 g, 1.04 mmol) and Lawesson's reagent (0.252 g, 0.624 mmol) in toluene (15 mL) within 12 h as described for the synthesis of 147a gave compound 153a (0.291 g, 94%) as yellow solid. 1H NMR (CDCl3, 400 MHz) δ 3.90 (3H, s), 6.04 (2H, s), 6.62-6.68 (2H, m), 7.38-7.42 (1H, m), 7.48 (2H, t, J=7.2), 7.68 (2H, d, J=8.0), 7.82 (1H, d, J=4.8), 8.53 (1H, s); 13C NMR (CDCl3, 100 MHz) δ 50.9, 56.4, 110.0, 112.0, 120.2, 122.4, 128.5, 129.3, 132.2, 136.4, 141.9, 158.7, 171.5 HRMS (EI) calcd for C15H14N4O2 [M]+ 282.1117. found 282.1115. HRMS (EI) calcd for C15H14N4OS [M]+ 298.0888. found 298.0888.

Sources & evidence

ORD record
ord-867d92e2f8444c0c8f45bbcf1d83730b
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Linked notes

Loading…