Lawesson's reagent → HCID 19047049, compound

HRID 1780590Notes

Reaction equation

HRID 1780590 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:9])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([C:7](=[S:23])[NH2:9])[CH:10]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 13244367HCID 13244367, compound

Product 1

HCID 19047049HCID 19047049, compoundYield 159.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.0 g (0.040 mol) of the product from Step A was suspended in toluene (140 mL). Lawesson's reagent (9.4 g, 0.023 mol) was added and the resulting mixture heated at 100° for 3 h (the mixture became homogeneous at 85° C.). After cooling to room temperature, the toluene was removed on the rotary evaporator. The residue was flash chromatographed on silica gel eluting with 20% ethyl acetate/hexane to furnish 7.2 g (95% yield) of the title compound as a yellow semisolid. 1H NMR (400 MHz, CDCl3) δ 7.92-7.94 (d,1H), 7.93 (br s, 1H, overlap with doublet), 7.25-7.32 (m,2H), 7.17 (br s, 1H), 2.45 (s,3H).

Workup

  1. temperaturethe resulting mixture heated at 100° for 3 h (the mixture
  2. custombecame homogeneous at 85° C.
  3. customthe toluene was removed on the rotary evaporator
  4. customchromatographed on silica gel eluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6d71133eef7943aba0fe4b55285c779f
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

Loading…