Methanesulfonic Acid → 5-Dimethylaminomethylfurfuryl chloride hydrochloride

HRID 1379893Notes

Reaction equation

HRID 1379893 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1[O:12][C:9]([CH2:10]O)=[CH:8][CH:7]=1)[CH3:4].S(Cl)([Cl:15])=O.CS(O)(=O)=O>C(#N)C>[ClH:15].[CH3:2][N:3]([CH2:5][C:6]1[O:12][C:9]([CH2:10][Cl:1])=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 24386Thionyl Chloride2×HCID 3086123((2-(Hydroxymethyl)-5-furyl)methyl)ammonium chloride

Product 1

HCID 129547925-Dimethylaminomethylfurfuryl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride (201 g, 1.05 mol) and acetonitrile (500 mL). Add dropwise, thionyl chloride (119 g, 1.0 mol) at such a rate that the temperature of the reaction is maintained at about 30° C. to 35° C. After the addition of thionyl chloride is complete, add methanesulfonic acid (144 g, 1.5 mol) while removing sulfur dioxide and acetonitrile by distillation. Stop the distillation when about 250 mL of distillate has been collected to give the title compound as a solution.

Workup

  1. additionAdd dropwise
  2. customwhile removing sulfur dioxide and acetonitrile
  3. distillationby distillation
  4. distillationthe distillation when about 250 mL of distillate
  5. customhas been collected

Sources & evidence

ORD record
ord-88d0520323934382803a9e351b4cb7bb
Source dataset
uspto-grants-1997_09
Patent number
US05672724

Reaction notes

Loading…