2,4-Dichlorobenzaldehyde → HCID 2872053, compound

HRID 980844Notes

Reaction equation

HRID 980844 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11](O)(=[S:15])[CH:12](C)O.[CH:17]([O-:19])=O.[NH4+:20]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]1[NH:20][C:17](=[O:19])[CH:11]([CH3:12])[S:15]1

Participants

5

Reactant 3

HCID 134042,4-DichlorobenzaldehydeHCID 2723923Ammonium formateHCID 178473673HCID 178473673, compound

Product 1

HCID 2872053HCID 2872053, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 500 ml 3-necked flask equipped with a Dean & Stark trap and reflux condenser, 30 g (0.17 mole) 2,4-dichlorobenzaldehyde, 18.2 g (0.17 mole) 95% thiolactic acid and 10.8 g (0.17 mole) ammonium formate in 150 ml toluene were placed. The reaction mixture was heated to reflux for several hours; 17 ml water collected. The mixture was at first clear in color and then turned yellow. The reaction mixture was allowed to sit overnight during which yellow solids precipitated. The mixture was filtered. The solids were washed with ether and then air dried to give 38 g of the above-identified product as a white solid.

Workup

  1. customIn a 500 ml 3-necked flask equipped with a Dean & Stark trap
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for several hours
  5. custom17 ml water collected
  6. customprecipitated
  7. filtrationThe mixture was filtered
  8. washThe solids were washed with ether
  9. customair dried

Sources & evidence

ORD record
ord-4a90b5d585b84a69abc30eb38845b60c
Source dataset
uspto-grants-1987_01
Patent number
US04639460

Reaction notes

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