Dimethylamine → HCID 19760943, compound

HRID 971956Notes

Reaction equation

HRID 971956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.O1CCOCC1.[CH3:26][NH:27][CH3:28]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([N:27]([CH3:28])[CH3:26])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 24386Thionyl ChlorideHCID 312751,4-DioxaneHCID 7266935-(4-Chlorophenyl)-2-furoic acid

Product 1

HCID 19760943HCID 19760943, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 58 g (0.26 mole) of 5-(4-chlorophenyl)-2-furoic acid and 120 ml of thionyl chloride was heated under reflux for 3 hrs. The thionyl chloride was removed on a rotary evaporator. A small amount of benzene was added to the residual solid and then removed on a rotary evaporator. The furoyl chloride was dissolved in 300 ml of dioxane with stirring and treated dropwise with a solution of 300 ml of dioxane containing 26 g (0.58 mole) of dimethylamine, while maintaining the temperature between 15°-25°. The reaction solution was stirred at room temperature overnight and then at 80° for 4 hrs. with a small amount of solid forming. The mixture was added to 2000 ml of water and resulting solid was filtered and dried at 60° to yield 58 g (77%). An analytical sample was prepared by recrystallizing a sample from hexane, m.p. 101°-102°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hrs
  3. customThe thionyl chloride was removed on a rotary evaporator
  4. additionA small amount of benzene was added to the residual solid
  5. customremoved on a rotary evaporator
  6. dissolutionThe furoyl chloride was dissolved in 300 ml of dioxane
  7. temperaturewhile maintaining the temperature between 15°-25°
  8. stirringThe reaction solution was stirred at room temperature overnight
  9. customwith a small amount of solid forming
  10. customresulting solid
  11. filtrationwas filtered
  12. customdried at 60°
  13. customto yield 58 g (77%)
  14. customAn analytical sample was prepared
  15. customby recrystallizing a sample from hexane, m.p. 101°-102°

Sources & evidence

ORD record
ord-e874de110c314855b410b20c7793f19d
Source dataset
uspto-grants-1979_07
Patent number
US04162257

Reaction notes

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