Lawesson's reagent → HCID 13054014, compound

HRID 1950667Notes

Reaction equation

HRID 1950667 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=O)=[CH:5][CH:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[S:30])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 3460444-methoxy-N-(4-nitrophenyl)benzamide

Product 1

HCID 13054014HCID 13054014, compoundYield 129.3%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 4-methoxy-4′-nitrothiobenzaniline 3 (1.0 g, 3.7 mmol) and Lawesson's reagent (0.89 g, 2.2 mmol, 0.6 equiv.) in chlorobenzene (15 mL) was heated to reflux for 4 hrs. The solvent was evaporated and the residue was purified with flush column (hexane:ethyl acetate=4:1) to give 820 mg (77.4%) of the product 4 as orange color solid. 1HNMR (300 MHz, DMSO-d6) δ: 8.29 (d, 2H, H-3′,5′), 8.00 (d, J=8.5 Hz, 2H, H-2′,6′), 7.76 (d, 2H), 7.03 (d, J=8.4 Hz, 2H), 3.808.37 (d, J=5.5 Hz, 2H, H-3′,5′), 8.17 (d, J=6.3 Hz, 2H, H-2′,6′), 7.48 (d, J=6.6 Hz, 2H), 6.97 (d, J=6.5 Hz, 2H), 3.75 (s, 3H, MeO). (s, 3H, MeO).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hrs
  3. customThe solvent was evaporated
  4. customthe residue was purified
  5. customwith flush column (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f336f553f9e34ec4917adca7b1c86b73
Source dataset
uspto-grants-2013_03
Patent number
US08404213B2

Reaction notes

Loading…