Methanesulfonic Acid → 5-Dimethylaminomethylfurfuryl chloride hydrochloride

HRID 1379895Notes

Reaction equation

HRID 1379895 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

Conditions

Temperature
10 °C

Procedure

Combine 5-[(dimethylamino)methyl]-furfuryl alcohol hydrochloride (1.72 kg, 8.97 mol) and acetonitrile (4.3 L). Cool to about 10° C. Add thionyl chloride (1.02 kg, 8.54 mol) dropwise, while maintaining the temperature of the reaction at below about 40° C. After the addition of thionyl chloride is complete, add methanesulfonic acid (1.3 kg, 13.5 mol). Distill to remove about 1.8 L of distillate to give the title compound as a solution.

Workup

  1. customthe temperature of the reaction at below about 40° C
  2. distillationDistill
  3. customto remove about 1.8 L of distillate

Sources & evidence

ORD record
ord-82f011ea3df240f298bd03a1f2836efc
Source dataset
uspto-grants-1997_09
Patent number
US05672724

Reaction notes

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