Benzylethanolamine → 2-(Benzylamino)ethyl hydrogen sulfate

HRID 1864005Notes

Reaction equation

HRID 1864005 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[C:6]1([CH2:12][NH:13][CH2:14][CH2:15][OH:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(O)C>[S:2]([OH:5])([O:16][CH2:15][CH2:14][NH:13][CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

6

Reactant 2

HCID 4348BenzylethanolamineHCID 24638Chlorosulfonic acid

Product 1

HCID 218250682-(Benzylamino)ethyl hydrogen sulfateYield 74%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

Chlorosulfonic acid (13.3 mL, 0.2 mol) was added very slowly to (2-[(phenylmethyl)amino]ethanol (30.2 g, 0.2 mol) in carbon tetrachloride (100 mL) in an ice bath. The resulting thick white suspension was stirred at room temperature overnight The suspension was diluted with chloroform and ethanol, warmed to 45° C. and then cooled in an ice bath. The precipitate was collected by filtration, washed with ethanol and dried under vacuum for 16 hrs at 40° C. to afford the desired compound (34 g, 74%). MS (ES)+ m/z 232 [M+H]+.

Workup

  1. temperaturewarmed to 45° C.
  2. temperaturecooled in an ice bath
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethanol
  5. customdried under vacuum for 16 hrs at 40° C.

Sources & evidence

ORD record
ord-ac5685c7b8084a4b95d5aebb6d9fb6d6
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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