Sulfuric Acid → HCID 54391790, compound

HRID 2255846Notes

Reaction equation

HRID 2255846 reaction equation
Cl[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[CH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[CH:5][CH:4]=1.NC(N)=[S:23].[OH-].[Na+].S(=O)(=O)(O)O>CCOCC.ClCCl.C(O)C>[SH:23][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([CH:7]=[CH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[O:17][CH3:18])=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 545377842-{2-[4-(Chloromethyl)phenyl]ethenyl}-1,4-dimethoxybenzene

Product 1

HCID 54391790HCID 54391790, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4'-chloromethyl-2,5-dimethoxystilbene (856 mg, 2.96 mmol), thiourea (0.29 g, 3.8 mmol), and ethanol (16 ml) was heated to reflux for 3.5 h. Aqueous sodium hydroxide (2.5 M, 2.8 ml) was added and the mixture refluxed for further 2 h. The reaction mixture was allowed to cool and dichloromethane (50 ml), ether (200 ml) and sulfuric acid (10%, 10 ml) were added. The organic layer was separated, washed with water (2×200 ml), brine (100 ml), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1) to give (32b) (328 mg, 39%); νmax /cm-1 2950s, 1490m, 1470s, 1430m, 1390s, 1215s, 1180s, 1050s.

Workup

  1. temperatureto reflux for 3.5 h
  2. temperaturethe mixture refluxed for further 2 h
  3. temperatureto cool
  4. customThe organic layer was separated
  5. washwashed with water (2×200 ml), brine (100 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography over silica (dichloromethane/hexane; 4:1)

Sources & evidence

ORD record
ord-95969d30a5794f3b8d23438ca248fa3b
Source dataset
uspto-grants-1997_08
Patent number
US05653914

Reaction notes

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