Methylamine → 2-Hydroxyphenyl methylsulfamate

HRID 1022728Notes

Reaction equation

HRID 1022728 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][S:2]1(=[O:11])=[O:10].[CH3:12][NH2:13]>C1COCC1.C(OCC)(=O)C>[CH3:12][NH:13][S:2](=[O:11])(=[O:10])[O:1][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[OH:3]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 37776671,3,2Lambda6-benzodioxathiole-2,2-dione

Product 1

HCID 669759552-Hydroxyphenyl methylsulfamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3,2-benzodioxathiol 2,2-dioxide (300 mg) in THF (6 mL) was added methylamine (0.871 mL, 2 M THF solution) at room temperature, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (86 mg).

Workup

  1. washThe diluted solution was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fec88b87266840f0870fc48372b7a6b2
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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