Lawesson's reagent → HCID 57678306, compound

HRID 491425Notes

Reaction equation

HRID 491425 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]2[C:17]([Br:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Br:19])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([C:9](=[S:31])[NH:11][C:12]2[C:17]([Br:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Br:19])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57678304HCID 57678304, compound

Product 1

HCID 57678306HCID 57678306, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-tert-butyl-N-(2,6-dibromophenyl)benzamide prepared as in Example 18 (1.20 g, 2.92 mmol) was dissolved in toluene (45 mL) and treated with Lawesson's reagent (1.18 g, 2.92 mmol.) The solution was heated to reflux for 2 h and then cooled. The solvent was removed under reduced pressure, and the residue was adsorbed onto silica gel. Elution with 10% to 20% acetone/hexane gave 0.509 g (41%) of product. MS (ESI) m/z 425.952; HPLC Method B, purity 85.7% at 210-370 nm, 11.1 min.; 91.1% at 262 nm, 11.1 min.; HRMS: calcd for C17H17Br2NS+H+, 425.95212; found (ESI, [M+H]+), 425.952.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperaturecooled
  4. customThe solvent was removed under reduced pressure
  5. washElution with 10% to 20% acetone/hexane

Sources & evidence

ORD record
ord-8f5b4aec34f74694ae219499ccce7f1f
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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