Lawesson's reagent → HCID 68380034, compound

HRID 2364965Notes

Reaction equation

HRID 2364965 reaction equation
Br[C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[S:16])[C:12]([F:15])([F:14])[F:13].BrC1C(OC)=CC=CC=1NC(=O)C(F)(F)F.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>O1CCOCC1>[F:13][C:12]([F:15])([F:14])[C:11]1[S:16][C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=2[N:10]=1

Participants

5

Reactant 3

HCID 87949Lawesson's reagentHCID 86671725HCID 86671725, compoundHCID 86671726HCID 86671726, compound

Product 1

HCID 68380034HCID 68380034, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Synthesis of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroethanethioamide (C25). A solution of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroacetamide (C24) (776 mg, 2.6 mmol) and Lawesson's reagent (1.07 g, 2.6 mmol) in 1,4-dioxane (13 mL) was heated to 135° C. overnight. The mixture was cooled to room temperature, filtered, and concentrated in vacuo. Purification via silica get chromatography (Gradient: 0% to 20% ethyl acetate in heptanes) afforded the title compound as an oil. Yield: 839 mg, 2.60 mmol, quantitative. LCMS m/z 314.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 3.95 (s, 3H), 6.92 (dd, J=8.3, 1.1 Hz, 1H), 7.39 (dd, J=8.4, 8.3 Hz, 1H), 8.28 (dd, J=8.2, 0.8 Hz, 1H), 9.75 (br s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification via silica
  4. customget chromatography (Gradient: 0% to 20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-81e565fca72a4696811abed85b52c22f
Source dataset
uspto-grants-2014_04
Patent number
US08697673B2

Reaction notes

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