Propanethioamide → HCID 67436210, compound

HRID 1496627Notes

Reaction equation

HRID 1496627 reaction equation
[C:1](=[S:5])([NH2:4])[CH2:2][CH3:3].Br.Br[CH:8]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O>CN(C=O)C>[CH2:2]([C:1]1[S:5][C:8]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[N:4]=1)[CH3:3]

Participants

4

Reactant 2

HCID 2760628PropanethioamideHCID 111647242-Bromo-1-(4-fluorophenyl)-2-(4-pyridyl)ethanone hydrobromide

Product 1

HCID 67436210HCID 67436210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 1.31 g (14.7 mmol) propanethioamide are added to a solution of 5.00 g (13.3 mmol) of 2-bromo-1-(4-fluorophenyl)-2-(4-pyridyl)ethanone hydrobromide (described, for example, in Chem. Pharm. Bull. 2005, 53, 410-418) in 30 ml of DMF, and the mixture is stirred for 16 h. Subsequently, the reaction mixture is stirred into 100 ml of ice-water, 50 ml of a saturated aqueous Na—HCO3 are added and the mixture is extracted with ethyl acetate (3×100 ml). The combined organic phases are washed with water (2×100 ml), dried over MgSO4 and freed from the solvent under reduced pressure. The crude product is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 2.85 g (75%) of the desired product; 1H-NMR (DMSO-d6) δ: 8.53 (d, 2H), 7.47 (m, 2H), 7.26 (d, 2H), 7.17 (m, 2H), 3.05 (q, 2H), 1.37 (t, 3H).

Workup

  1. customAt room temperature
  2. additionare added
  3. extractionthe mixture is extracted with ethyl acetate (3×100 ml)
  4. washThe combined organic phases are washed with water (2×100 ml)
  5. dry with materialdried over MgSO4
  6. customThe crude product is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-2e8b1f59593e426795160b875e203eeb
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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