Sodium Hydroxide → 3-dipropylamino-5-chloroformylchroman-HCL

HRID 37648Notes

Reaction equation

HRID 37648 reaction equation
[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](OC)=[O:16])[O:7][CH2:6]1)[CH2:2][CH3:3].[OH-].[Na+].O=S(Cl)[Cl:26]>CO.O>[ClH:26].[CH2:1]([N:4]([CH2:19][CH2:20][CH3:21])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15]([Cl:26])=[O:16])[O:7][CH2:6]1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 190280933-Dipropylamino-5-methyloxycarbonylchroman

Product 1

HCID 190280833-dipropylamino-5-chloroformylchroman-HCLYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Dipropylamino-5-methyloxychroman (Example 2; 400 mg, 1.37 mmol) was dissolved in 10 ml methanol and NaOH (60 mg, 1.5 mmol) in 2 mL H2O was added. The mixture was refluxed for 5 hours, cooled, filtered through Celite and evaporated to dryness. The residue was refluxed in SOCl2 (5 mL, 68 mmol) for 30 minutes. The excess SOCl2 was then removed in vacuo to give 3-dipropylamino-5-chloroformylchroman-HCL as a gum. The pale brown gum was dissolved in CH2Cl2 (50 mL), and a stream of NH3 (g) was introduced during 2 minutes. The solution was washed with aqueous NaHCO3, dried with Na2SO4 and evaporated to dryness. The oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:4. Yield 80%, 13C-NMR: 172.0 154.9 136.5 126.9 120.4 119.1 118.6 67.8 53.0 52.6 26.1 22.4 21.9 14.1 11.7.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. customevaporated to dryness
  5. customThe excess SOCl2 was then removed in vacuo

Sources & evidence

ORD record
ord-dc8dd51deb8d412f8dc1aac4e7add5ec
Source dataset
uspto-grants-1995_05
Patent number
US05420151

Reaction notes

Loading…