Potassium Carbonate → HCID 14459966, compound

HRID 346206Notes

Reaction equation

HRID 346206 reaction equation
[C:1]1([CH2:7][CH2:8][SH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]1([CH2:7][CH2:8][S:9][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 781262-Phenylethanethiol

Product 1

HCID 14459966HCID 14459966, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-phenylethylmercaptan (72.3 mmol, 10.0 g), 4-bromobenzaldehyde (79.6 mmol, 14.7 g) and potassium carbonate (116 mmol, 16 g) were stirred in dimethylformamide (100 ml) at 110° C. for 48 hours. The solution was cooled and diluted with water (200 ml). The aqueous was extracted with ether (3×200 ml) and the combined ether layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified on silica gel using hexane:ethyl acetate (9:1) as eluant to afford 11.7 g (67%) of present title product as a yellow oil. 1H-NMR(CDCl3)delta(ppm): 3.1 (d of t), 7.2 (s), 7.3 (d), 7.7 (d), 9.9 (s). MS (m30 ) 242.

Workup

  1. temperatureThe solution was cooled
  2. extractionThe aqueous was extracted with ether (3×200 ml)
  3. dry with materialthe combined ether layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-503e97a6fa3a40c880d4afee0cc00602
Source dataset
uspto-grants-1991_10
Patent number
US05061717

Reaction notes

Loading…