Water → HCID 57471692, compound

HRID 1496628Notes

Reaction equation

HRID 1496628 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[C:12]([NH2:16])(=[S:15])[CH2:13][CH3:14].O>C(O)C>[CH2:13]([C:12]1[S:15][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:16]=1)[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 2760628Propanethioamide

Product 1

HCID 57471692HCID 57471692, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.40 g (11.0 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone and 1.00 g (11.0 mmol) of thiopropanamide in 50 ml of ethanol is stirred under reflux for 2 h and at room temperature for 16 h. The reaction mixture is stirred into 200 ml of water and extracted with ethyl acetate (3×100 ml). The combined organic phases are washed with 50 ml of water, dried over MgSO4 and freed from the solvent under reduced pressure. This gives 2.05 g (87%) of the desired product; 1H-NMR(DMSO-d6) δ: 7.99 (m, 2H), 7.92 (s, 1H), 7.26 (m, 2H), 3.04 (q, 2H), 1.34 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe combined organic phases are washed with 50 ml of water
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-19c620b8cc7f4eefbd6ca3d0cbe4fe5e
Source dataset
uspto-grants-2015_12
Patent number
US09198426B2

Reaction notes

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