Lawesson's reagent → HCID 83390150, compound

HRID 880992Notes

Reaction equation

HRID 880992 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7]([NH:9][CH3:10])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH:11]=1)[C:7](=[S:22])[NH:9][CH3:10]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 24696192HCID 24696192, compound

Product 1

HCID 83390150HCID 83390150, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-2-fluoro-N-methylbenzamide (500 mg, 2 mmol) and Lawesson's reagent (872 mg, 2.16 mmol) in toluene (10 mL) was heated to 100° C. and stirred for 3.5 hours. The reaction was cooled to room temperature, diluted with toluene, and filtered. The filtrate was concentrated and purified by flash column chromatography (0-20% ethyl acetate/heptanes) to give the title compound (494 mg, 92%) as a yellow oil that solidified upon standing. +ESI (M+H+1) 250.1; 1H NMR (400 MHz, CDCl3, δ): 8.20 (dd, J=6.93, 2.63 Hz, 1H), 8.06 (br.s., 1H), 7.47 (ddd, J=8.73, 4.44, 2.63 Hz, 1H), 6.95 (dd, J=11.12, 8.78 Hz, 1H), 3.32 (dd, J=4.88, 0.78 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash column chromatography (0-20% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-7ee8e83dbce249aab06e9b0cf6529de0
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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