Methanesulfonic Acid → HCID 19750881, compound

HRID 1659576Notes

Reaction equation

HRID 1659576 reaction equation
CS(O)(=O)=O.[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15][OH:16])=[CH:12][CH:11]=1)[CH3:8].[NH2:17][CH2:18][CH2:19][CH2:20]O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:17][CH2:18][CH2:19][CH2:20][O:16][CH2:15][C:13]1[O:14][C:10]([CH2:9][N:7]([CH3:6])[CH3:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 90863-Amino-1-propanolHCID 10340Sodium CarbonateHCID 849065-((Dimethylamino)methyl)-2-furanmethanol

Product 1

HCID 19750881HCID 19750881, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of methanesulphonic acid (18 ml) in dry tetrahydrofuran (40 ml) kept at room temperature was added, with stirring, a mixture of 5-[(dimethylamino)methyl]-2-furanmethanol (4.65 g) and 3-amino-1-propanol (6.75 g). After 3 days the suspension was heated on a steam bath for 30 mins. Excess anhydrous sodium carbonate and ethyl acetate (100 ml) were added and the heating continued for 20 mins. The hot suspension was filtered and the residue washed with hot ethyl acetate (3×50 ml). The combined filtrates were evaporated to dryness, water (150 ml) added and the solution extracted with ethyl acetate (3×50 ml). The aqueous fraction was acidified with oxalic acid (5 g) and the solution evaporated to low bulk. Ethyl acetate (100 ml) and excess anhydrous sodium carbonate were added and the suspension heated to boiling point for 30 mins. The hot suspension was filtered and the combined filtrates and washings evaporated to dryness. The oily residue was distilled (100°-110°/0.2 mm) to give the title compound (2.76 g).

Workup

  1. customkept at room temperature
  2. additionwas added
  3. temperatureAfter 3 days the suspension was heated on a steam bath for 30 mins
  4. filtrationThe hot suspension was filtered
  5. washthe residue washed with hot ethyl acetate (3×50 ml)
  6. customThe combined filtrates were evaporated to dryness, water (150 ml)
  7. additionadded
  8. extractionthe solution extracted with ethyl acetate (3×50 ml)
  9. customthe solution evaporated to low bulk
  10. additionEthyl acetate (100 ml) and excess anhydrous sodium carbonate were added
  11. temperaturethe suspension heated
  12. customfor 30 mins
  13. filtrationThe hot suspension was filtered
  14. customthe combined filtrates and washings evaporated to dryness
  15. distillationThe oily residue was distilled (100°-110°/0.2 mm)

Sources & evidence

ORD record
ord-ed18bd4451c041ebb45b0798d3c5580e
Source dataset
uspto-grants-1981_12
Patent number
US04304780

Reaction notes

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