Lawesson's reagent → HCID 58316709, compound

HRID 1426229Notes

Reaction equation

HRID 1426229 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=O)[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:24])=CC=1>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[S:24])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 17100900N-(5-Iodopyridin-2-yl)-2,2-dimethylpropanamide

Product 1

HCID 58316709HCID 58316709, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

N-(5-Iodo-pyridin-2-yl)-2,2-dimethyl-propionamide (example 39, step 1) (5.8 g, 19.1 mmol) was dissolved in 30 ml of toluene and Lawesson's reagent (7.7 g, 19.1 mmol, 1 equiv.) was added at room temperature. The reaction mixture was stirred for 48 hours at 110° C. The crude product was purified by flash chromatography by directly loading the cooled toluene reaction mixture onto a 300 g silica gel column and eluting with heptane:ethyl acetate 100:0→80:20. The desired N-(5-iodo-pyridin-2-yl)-2,2-dimethyl-thiopropionamide was obtained as a yellow oil (5.1 g, 75% yield), MS: m/e=321.0 (M+H+).

Workup

  1. customThe crude product was purified by flash chromatography
  2. customthe cooled toluene reaction mixture onto a 300 g silica gel column
  3. washeluting with heptane:ethyl acetate 100:0→80:20

Sources & evidence

ORD record
ord-f1e916b8cb114143b1cfccb2b82df47e
Source dataset
uspto-grants-2015_01
Patent number
US08933094B2

Reaction notes

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