Dimethylformamide → Benzaldehyde, p-phenylthio-

HRID 130631Notes

Reaction equation

HRID 130631 reaction equation
CN(C)C=O.[C:6]1([SH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1>O>[C:6]1([S:12][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77264-ChlorobenzaldehydeHCID 7969ThiophenolHCID 10340Sodium Carbonate

Product 1

HCID 71023Benzaldehyde, p-phenylthio-Yield 28.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a dimethylformamide (DMF) solution (30 mL) of 11.0 g (100 mmol) of benzenethiol is gradually added 14.0 g (132 mmol) of anhydrous Na2CO3 at 85° C. Then 4-chlorobenzaldehyde (11.3 g, 80.0 mol) is added during 20 min. at 85° C. The reaction solution is stirred at this temperature for 3 h. After adding H2O into the reaction mixture, the crude product is extracted with ethyl acetate. The organic layer is washed twice with H2O and with brine, dried over anhydrous MgSO4 and condensed. The residue is applied to column chromatography on silica gel with acetone-hexane (from 1:30 to 1:10) as eluent. 6.05 g of pale yellow oil are obtained (35%). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 7.24 (d, 2H), 7.42-7.44 (m, 3H), 7.53 (dd, 2H), 7.71 (d, 2H), 9.96 (s, 1 H).

Workup

  1. customat 85° C
  2. extractionthe crude product is extracted with ethyl acetate
  3. washThe organic layer is washed twice with H2O and with brine
  4. dry with materialdried over anhydrous MgSO4 and condensed

Sources & evidence

ORD record
ord-12506bf2fbf64174a502d119d2e292f3
Source dataset
uspto-grants-2008_06
Patent number
US07381842B2

Reaction notes

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