Tetrabutylammonium Periodate → HCID 178510499, compound

HRID 485268Notes

Reaction equation

HRID 485268 reaction equation
[NH2:1]/[C:2](/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:3]1\[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[S:7]\1.I([O-])(=O)(=O)=[O:20].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[NH2:1]/[C:2](/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:3]1\[C:4](=[O:12])[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[S:7]\1=[O:20]

Participants

4

Reactant 2

HCID 2724292Tetrabutylammonium PeriodateHCID 178510717HCID 178510717, compound

Product 1

HCID 178510499HCID 178510499, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.6 gm (0.003 mol) of (E)-2-[(amino)phenylmethylene]-benzo[b]thiophen-3(2H)-one and 13.75 gm (0.03 mol) of tetrabutylammonium periodate (prepared from tetrabutylammonium hydrogen sulfate and sodium metaperiodate in water) in 50 ml of dichloromethane were refluxed for about 2 hours. After the end of the reaction, which was monitored by thin-layer chromatography, the mixture was allowed to cool and was then filtered through a column of silicagel (200 gm), finally using dichloromethane/ethyl acetate (97:3 v/v) as the eluant. By evaporating the appropriate fractions and subsequently recrystallizing the residue from ethanol, 5.8 gm (72% of theory) of pale yellow crystals, m.p. 246°-247° C. (decomposition), were obtained.

Workup

  1. customAfter the end of the reaction, which
  2. temperatureto cool
  3. filtrationwas then filtered through a column of silicagel (200 gm), finally using dichloromethane/ethyl acetate (97:3 v/v) as the eluant
  4. customBy evaporating the appropriate fractions
  5. customsubsequently recrystallizing the residue from ethanol, 5.8 gm (72% of theory) of pale yellow crystals, m.p. 246°-247° C. (decomposition)
  6. customwere obtained

Sources & evidence

ORD record
ord-7e5a97d881cb4acf92ffa1412a386f9b
Source dataset
uspto-grants-1985_08
Patent number
US04536402

Reaction notes

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