Thionyl Chloride → 5-Dimethylaminomethylfurfuryl chloride hydrochloride

HRID 1379891Notes

Reaction equation

HRID 1379891 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:11][C:8]([CH2:9]O)=[CH:7][CH:6]=1)[CH3:3].S(Cl)([Cl:14])=O>ClCCl>[ClH:14].[CH3:1][N:2]([CH2:4][C:5]1[O:11][C:8]([CH2:9][Cl:14])=[CH:7][CH:6]=1)[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 849065-((Dimethylamino)methyl)-2-furanmethanol

Product 1

HCID 129547925-Dimethylaminomethylfurfuryl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Combine 5-[(dimethylamino)methyl]-furfuryl alcohol (25 g) and dichloromethane (100 mL). Cool to 0° C. Add dropwise, thionyl chloride (20 mL) at such a rate that the reaction does not rise above 5° C. After 0.5 hours, evaporate in vacuo to give a residue, Recrystallize the residue from ethanol to give the title compound: mp; 164°-165° C. (dec).

Workup

  1. additionAdd dropwise
  2. customdoes not rise above 5° C
  3. customevaporate in vacuo
  4. customto give a residue
  5. customRecrystallize the residue from ethanol

Sources & evidence

ORD record
ord-f93bd4428c1f4917982bfad123bb99b3
Source dataset
uspto-grants-1997_09
Patent number
US05672724

Reaction notes

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