Dabco → HCID 86660140, compound

HRID 1746228Notes

Reaction equation

HRID 1746228 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].[CH3:12][N:13]([CH3:17])[C:14](Cl)=[S:15].C1N2CCN(CC2)C1>CN(C=O)C>[C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[O:8][C:14](=[S:15])[N:13]([CH3:17])[CH3:12])(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 27373241-(2-fluoro-6-hydroxyphenyl)ethanone

Product 1

HCID 86660140HCID 86660140, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-Fluoro-6-hydroxy-phenyl)-ethanone (2.5 g, 16.22 mmol) (available from Apollo Scientific) was dissolved in anhydrous DMF (20 mL.) Dimethylthiocarbamoyl chloride (2.2 g, 17.84 mmol) and DABCO (2.0 g, 17.84 mmol) were added sequentially in one portion. The reaction was permitted to stir overnight at ambient temperature. The reaction was quenched by pouring it into a mixture of 1N HCl-ice. The oily residue was extracted with dichloromethane and dried over sodium sulfate. The crude residue was purified by SGC (20% ethyl acetate in hexanes) to provide the title compound (2.93 g.) 1H NMR (200 MHz, CDCl3): δ (ppm)=7.407 (dd, 1H), 7.026 (t, 1H), 6.876 (d, 1H), 3.404 (s, 3H), 3.341 (sd, 3H), 2.58 (d, 3H).

Workup

  1. additionwere added sequentially in one portion
  2. customThe reaction was quenched
  3. additionby pouring it
  4. additioninto a mixture of 1N HCl-ice
  5. extractionThe oily residue was extracted with dichloromethane
  6. dry with materialdried over sodium sulfate
  7. customThe crude residue was purified by SGC (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ba69be049e5045a5a4a0e703f5c5db19
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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