Beta-Alanine → N-(methylsulfonyl)-beta-alanine

HRID 1731875Notes

Reaction equation

HRID 1731875 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH3:7][S:8](Cl)(=[O:10])=[O:9]>[OH-].[Na+]>[CH3:7][S:8]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 239Beta-AlanineHCID 31297Methanesulfonyl chloride

Product 1

HCID 6502032N-(methylsulfonyl)-beta-alanine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

22.3 g of β--alanine are dissolved in 125 ml of 2N NaOH. 20 ml of methanesulfonyl chloride and 145 ml of 2N NaOH are simultaneously added dropwise at 0°-5° C., with vibromixing, and the mixture is vibrated at room temperature for 3 hours. The solution is extracted with ether and the extract is diluted to 400 ml and stirred with a strongly acid ion exchanger (Lewatit® S 100) until the pH reaches about 2. The solution is then evaporated to dryness in vacuo. The residue is taken up in ethyl acetate, the mixture is dried over sodium sulfate and DCA is added until an alkaline reaction is obtained. The precipitate which separates out is filtered off, washed with ethyl acetate and ether, dried and recrystallized from tetrahydrofuran.

Workup

  1. extractionThe solution is extracted with ether
  2. additionthe extract is diluted to 400 ml
  3. customThe solution is then evaporated to dryness in vacuo
  4. dry with materialthe mixture is dried over sodium sulfate and DCA
  5. additionis added until an alkaline reaction
  6. customis obtained
  7. filtrationThe precipitate which separates out is filtered off
  8. washwashed with ethyl acetate and ether
  9. customdried
  10. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-af70c0d599574f7db10aec6fbad6e543
Source dataset
uspto-grants-1986_11
Patent number
US04623715

Reaction notes

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