Hydrochloric Acid → 2-(Methanesulfonyl)benzylamine hydrochloride

HRID 1819494Notes

Reaction equation

HRID 1819494 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([CH3:18])(=[O:17])=[O:16])(C)(C)C.[ClH:20]>O1CCOCC1.C(Cl)(Cl)Cl>[ClH:20].[CH3:18][S:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][NH2:7])(=[O:16])=[O:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22464527(2-Methanesulfonyl-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 162183342-(Methanesulfonyl)benzylamine hydrochlorideYield 89.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

(2-Methanesulfonyl-benzyl)-carbamic acid tert-butyl ester (1.55 g, 5.43 mmol) was dissolved in warm dioxane (50 mL) and cooled to room temperature. HCl solution (4M solution in dioxane, 20 ml, 80 mmol) was added. After 20 h, a white precipitate had formed. The reaction was diluted with CHCl3 (50 mL) and filtered. The white solid was washed with CHCl3 and dried in-vacuo to yield 1.075g of 2-methanesulfonyl-benzylamine hydrochloride as an off white solid, m/z 186.6 (M+1)+.

Workup

  1. customa white precipitate had formed
  2. filtrationfiltered
  3. washThe white solid was washed with CHCl3
  4. customdried in-vacuo

Sources & evidence

ORD record
ord-9a10e61025534704825a2a2dc82d2516
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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