Acetone → HCID 118513274, compound

HRID 1478815Notes

Reaction equation

HRID 1478815 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:15]=[CH:14][C:7]2[NH:8][C:9](=[S:13])[CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.[OH-].[K+].[CH3:20]C(C)=O>>[CH3:20][S:13][C:9]1[CH2:10][CH2:11][CH2:12][C:6]2[CH:5]=[C:4]([O:3][C:2]([F:1])([F:16])[F:17])[CH:15]=[CH:14][C:7]=2[N:8]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 118513289HCID 118513289, compound

Product 1

HCID 118513274HCID 118513274, compound

Procedure

To a solution of 7-(trifluoromethoxy)-4,5-dihydro-1H-benzo[b]azepine-2(3H)-thione (22 g, 84.3 mmol) in acetone (1500 ml) was added KOH (7.1 g, 127 mmol) and Mel (18.1 g, 127 mmol) and the mixture was stirred at RT for 1 h. The resulting mixture was concentrated under reduced pressure and the crude product was dissolved in DCM (1000 mL). The mixture was washed with water, brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow oil. The oil was purified by flash column chromatography on neutral aluminium oxide eluting with hexane to give the title compound.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. dissolutionthe crude product was dissolved in DCM (1000 mL)
  3. washThe mixture was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow oil
  8. customThe oil was purified by flash column chromatography on neutral aluminium oxide eluting with hexane

Sources & evidence

ORD record
ord-7cc8a72f1af7408593cb415da4eef4bf
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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