Methanesulfonic Acid → HCID 86740155, compound

HRID 1248411Notes

Reaction equation

HRID 1248411 reaction equation
CS(O)(=O)=O.[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13](CO)=[CH:12][CH:11]=1)[CH3:8].[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].[C:23](=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:11]1[CH:12]=[CH:13][O:14][C:10]=1[CH2:9][N:7]([CH3:6])[CH3:8]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 10340Sodium CarbonateHCID 258684-Amino-1-butanolHCID 849065-((Dimethylamino)methyl)-2-furanmethanol

Product 1

HCID 86740155HCID 86740155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methanesulphonic acid (86 g), 5-[(dimethylamino)methyl]-2-furanmethanol (15.52 g), and 4-aminobutanol (17.82 g) in tetrahydrofuran (100 ml) was heated at 98°-100° for 1.5 h. After 1 h. at room temperature, excess anhydrous sodium carbonate was added and the suspension filtered after 18 h. The filtrate was evaporated, water (230 ml) added and the suspension extracted with ether (3×80 ml). The ethereal extracts were washed with water (2×50 ml), the aqueous fraction acidified with oxalic acid (25 g) and evaporated to low bulk. Excess anhydrous sodium carbonate and ethyl acetate (200 ml) were added, the suspension heated at boiling for 30 min. and the suspension filtered after 2 h. Evaporation of the filtrate yielded an oil which was distilled (100°-110°/0.08 mm) to give the title compound (6.64 g).

Workup

  1. filtrationthe suspension filtered after 18 h
  2. customThe filtrate was evaporated
  3. additionwater (230 ml) added
  4. extractionthe suspension extracted with ether (3×80 ml)
  5. washThe ethereal extracts were washed with water (2×50 ml)
  6. customevaporated to low bulk
  7. additionExcess anhydrous sodium carbonate and ethyl acetate (200 ml) were added
  8. temperaturethe suspension heated
  9. waitat boiling for 30 min.
  10. filtrationthe suspension filtered after 2 h
  11. customEvaporation of the filtrate
  12. customyielded an oil which
  13. distillationwas distilled (100°-110°/0.08 mm)

Sources & evidence

ORD record
ord-9ad6cdf99efc47b7bc35bec835250a93
Source dataset
uspto-grants-1985_06
Patent number
US04524071

Reaction notes

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