Sodium Chloride → N-benzyl-N-methyl-ethanolamine methanesulfonate

HRID 983653Notes

Reaction equation

HRID 983653 reaction equation
[CH2:1]([N:8]([CH3:12])[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:15][S:16](Cl)(=[O:18])=[O:17].[Na+].[Cl-]>O.C1(C)C=CC=CC=1>[CH3:15][S:16]([O:11][CH2:10][CH2:9][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:12])(=[O:18])=[O:17]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 66876N-Benzyl-N-methylethanolamine

Product 1

HCID 12135708N-benzyl-N-methyl-ethanolamine methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

N-Benzyl-N-methyl-ethanolamine (20.73 g), 61.94 g of toluene and 83.41 g of a 30% aqueous solution of NaOH were respectively weighed and placed in a 300-mL four-necked flask. While the mixture was stirred, the flask inside temperature was lowered to 6.8° C. Then, 31.68 g of methanesulfonyl chloride was added dropwise over 3 hours and 17 minutes at a flask inside temperature of 5 to 10° C. Water (33 mL) was added to dissolve the NaCl which had precipitated out in the aqueous phase, and the mixture was separated into the toluene phase and aqueous phase. A toluene solution of N-benzyl-N-methyl-ethanolamine methanesulfonate was thus obtained in a yield of 68.8 mole percent.

Workup

  1. customplaced in a 300-mL four-necked flask
  2. customwas lowered to 6.8° C
  3. customhad precipitated out in the aqueous phase
  4. customthe mixture was separated into the toluene phase and aqueous phase

Sources & evidence

ORD record
ord-b2c4b0f8552f4d939ca1a8bf8384df0e
Source dataset
uspto-grants-2005_03
Patent number
US06864372B2

Reaction notes

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