2-Propanethiol → HCID 118093117, compound

HRID 708872Notes

Reaction equation

HRID 708872 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][CH:15]([SH:17])[CH3:16]>CN(C=O)C.CCOC(C)=O>[F:10][C:9]1[C:2]([S:17][CH:15]([CH3:16])[CH3:14])=[C:3]([CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=1)[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 63642-PropanethiolHCID 53416146HCID 53416146, compound

Product 1

HCID 118093117HCID 118093117, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 11A (51 mg, 0.273 mmol) in DMF (1 mL), were added TEA (0.057 mL, 0.409 mmol) and propane-2-thiol (0.030 mL, 0.327 mmol). The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with H2O (2×), 10% LiCl and brine, dried (Na2SO4), filtered though a 1″ pad of SiO2 and concentrated to give 20A (64 mg, 0.263 mmol, 97% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 10.69 (1H, s), 8.57 (1H, dd, J=2.4, 1.1 Hz), 8.15 (1H, dd, J=8.5, 2.5 Hz), 3.72 (1H, dt, J=13.4, 6.7 Hz), 1.33 (6H, d, J=6.0 Hz).

Workup

  1. washThe organic phase was washed with H2O (2×), 10% LiCl and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered though a 1″ pad of SiO2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-004db3c93a6240b79a458ef2cea97344
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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