Thionyl Chloride → HCID 24777734, compound

HRID 1170475Notes

Reaction equation

HRID 1170475 reaction equation
S(Cl)([Cl:3])=O.[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][N:15]([CH3:19])[CH2:16][CH2:17]O)=[CH:13][C:8]=2[O:7][CH2:6]1>C(Cl)Cl>[ClH:3].[O:5]1[C:9]2[CH:10]=[CH:11][C:12]([CH2:14][N:15]([CH2:16][CH2:17][Cl:3])[CH3:19])=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 974060HCID 974060, compound

Product 1

HCID 24777734HCID 24777734, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (60 mL) is added dropwise over 30 minutes to a 0° C. solution of 2-(benzo[1,3]dioxol-5-ylmethyl-methyl-amino)-ethanol (22.2 g, 110 mmol) in DCM (250 mL) under nitrogen. The ice bath is removed, and the solution is stirred at room temperature overnight (16 h). The white slurry is concentrated under reduced pressure, diluted with brine (150 mL) and ethyl acetate (200 mL), and the precipitate is collected via vacuum filtration. The solid is washed with ethyl acetate and dried overnight under vacuum to afford 26.5 g (91%) of benzo[1,3]dioxol-5-ylmethyl-(2-chloro-ethyl)-methyl-amine hydrochloride as a white powder.

Workup

  1. customThe ice bath is removed
  2. concentrationThe white slurry is concentrated under reduced pressure
  3. additiondiluted with brine (150 mL) and ethyl acetate (200 mL)
  4. filtrationthe precipitate is collected via vacuum filtration
  5. washThe solid is washed with ethyl acetate
  6. customdried overnight under vacuum

Sources & evidence

ORD record
ord-d19c8f69bfba476289d2d45eb8221c6f
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

Loading…