Thionyl Chloride → HCID 19915720, compound

HRID 1032679Notes

Reaction equation

HRID 1032679 reaction equation
[CH3:1][N:2]([CH2:14][CH:15](O)[CH3:16])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.S(Cl)([Cl:20])=O>>[CH3:1][N:2]([CH2:14][CH:15]([Cl:20])[CH3:16])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19915728HCID 19915728, compound

Product 1

HCID 19915720HCID 19915720, compound

Procedure

Thionyl chloride (50 ml) was added dropwise with stirring and cooling in an ice/water bath to 1-(N-methyl-N-(4-nitrophenethyl)amino)-2-hydroxypropane (1.5 g). After stirring at room temperature for 1 hour, the solution was refluxed on a steam bath for a further 2 hours. The solution was evaporated to dryness and the residual oil partitioned between 2N aqueous sodium carbonate solution and ethyl acetate. After two further extractions with ethyl acetate, the organic portions were combined, washed with a saturated brine solution, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness. The resultant brown oil was chromatographed on silica ("Kieselgel 60"- Trade Mark) eluting with ethyl acetate followed by collection and evaporation of suitable fractions to give the title compound as a yellow oil, (0.75 g).

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. temperaturethe solution was refluxed on a steam bath for a further 2 hours
  3. customThe solution was evaporated to dryness
  4. customthe residual oil partitioned between 2N aqueous sodium carbonate solution and ethyl acetate
  5. extractionAfter two further extractions with ethyl acetate
  6. washwashed with a saturated brine solution
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe resultant brown oil was chromatographed on silica ("Kieselgel 60"- Trade Mark)
  11. washeluting with ethyl acetate
  12. customfollowed by collection and evaporation of suitable fractions

Sources & evidence

ORD record
ord-2e8030a2e31343fd9366e264a728af7d
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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