Sulfamide → Sulfamic acid chroman-2-ylmethyl amine

HRID 533440Notes

Reaction equation

HRID 533440 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][NH2:12].[S:13](N)([NH2:16])(=[O:15])=[O:14]>O1CCOCC1>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][NH:12][S:13]([NH2:16])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 112636861-(3,4-dihydro-2H-1-benzopyran-2-yl)methanamine

Product 1

HCID 11230247Sulfamic acid chroman-2-ylmethyl amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The oily amine (1.63 g, 10 mmol) and sulfamide (1.92 g, 20 mmol) were combined in dioxane (50 mL) and brought to reflux for 2 h. The solution was cooled and evaporated in vacuo to yield an oil, which was purified via column chromatography (DCM:Methanol 10:1) to yield a white solid. The solid was recrystallized from ethyl acetate/hexane to yield chroman-2-ylmethylsulfamide as a white solid.

Workup

  1. temperatureto reflux for 2 h
  2. temperatureThe solution was cooled
  3. customevaporated in vacuo
  4. customto yield an oil, which
  5. customwas purified via column chromatography (DCM:Methanol 10:1)
  6. customto yield a white solid
  7. customThe solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-3fff68b940ac4408aee17d7da6a3f729
Source dataset
uspto-grants-2014_10
Patent number
US08853263B2

Reaction notes

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