Lawesson's reagent → HCID 71139600, compound

HRID 539521Notes

Reaction equation

HRID 539521 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:22]=[CH:21][C:10]([CH2:11][N:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]3=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:22]=[CH:21][C:10]([CH2:11][N:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[C:13]3=[S:32])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 71138807HCID 71138807, compound

Product 1

HCID 71139600HCID 71139600, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Reaction of 146i (0.13 g, 0.45 mmol) and Lawesson's reagent (0.11 g, 0.27 mmol) in toluene according to method described for synthesis of 147a afforded 104 mg of 147i (76%) as yellow solid with greenish tinge. 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=5.9 Hz, 2H), 7.55 (d, J=8.3 Hz, 2H), 7.39 (m, 5H), 6.67 (dd, J=7.8, 1.1 Hz, 1H), 6.58 (dd, J=73, 6.7 Hz, 1H), 5.95 (s, 2H), 3.89 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 173.29, 159.15, 150.11, 147.43, 137.67, 136.17, 131.78, 128.58, 127.28, 121.35, 111.72, 109.67, 58.54, 56.66. HRMS (EI) calcd for C18H16N2OS [M]+ 308.0983. found 308.0975.

Sources & evidence

ORD record
ord-1eb0628f59354c08994c1d300ccfdeb3
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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