Hydrochloric Acid → HCID 18933620, compound

HRID 1598317Notes

Reaction equation

HRID 1598317 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[H-].[Na+].[CH2:13]([N:20]([CH2:22][CH2:23]Cl)[CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CN(C=O)C.C1(C)C=CC=CC=1.[OH-].[Na+].CCOCC>[CH2:13]([N:20]([CH2:22][CH2:23][O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])[CH3:21])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 313Hydrochloric Acid2×HCID 124815-Chloro-salicylaldehydeHCID 24758Sodium hydrideHCID 31968N-benzyl-2-chloro-N-methylethanamine

Product 1

HCID 18933620HCID 18933620, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-chloro-2-hydroxybenzaldehyde (25.68 g) in dry DMF (100 ml) was added dropwise to a stirred suspension of sodium hydride (6.84 g of a 60% dispersion in mineral oil) in dry DMF (100 ml) at ambient temperature under nitrogen with stirring. The mixture was heated on a steam bath for 1.5 hours, then cooled to ambient temperature and a solution of N-benzyl-2-chloro-N-methylethylamine in toluene (60 ml) [prepared by dissolving the hydrochloride (48.5 g) in 2M sodium hydroxide solution (50 ml) and extracting with toluene (2×30 ml) with drying] and the resulting mixture was heated on a steam bath for 4 hours. The mixture was cooled to ambient temperature and then poured into ice/water (100 ml). The mixture was extracted with ether and the combined ether extracts were washed with 2M sodium hydroxide solution until the washes were colourless. The ether extracts were then washed with 2M hydrochloric acid. The acidic extracts were basified with concentrated sodium hydroxide solution and extracted with dichloromethane to give an oil. A portion of the oil was dissolved in ether and treated with ethereal hydrogen chloride. The solid which precipitated was collected by filtration and recrystallised from propan-2-ol to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-chlorobenzaldehyde, m.p. 154°-155° C.

Workup

  1. temperatureThe mixture was heated on a steam bath for 1.5 hours
  2. extractionextracting with toluene (2×30 ml)
  3. customwith drying] and the resulting mixture
  4. temperaturewas heated on a steam bath for 4 hours
  5. temperatureThe mixture was cooled to ambient temperature
  6. additionpoured into ice/water (100 ml)
  7. extractionThe mixture was extracted with ether
  8. washthe combined ether extracts were washed with 2M sodium hydroxide solution until the washes
  9. washThe ether extracts were then washed with 2M hydrochloric acid
  10. extractionextracted with dichloromethane
  11. customto give an oil
  12. customThe solid which precipitated
  13. filtrationwas collected by filtration
  14. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-443d21b2b9214794afabd96bac912305
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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