2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethanamine → 2-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-ethylsulfamide

HRID 533443Notes

Reaction equation

HRID 533443 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][CH2:12][NH2:13].[S:14](N)([NH2:17])(=[O:16])=[O:15]>O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][CH2:12][NH:13][S:14]([NH2:17])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 556482-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethanamineHCID 82267Sulfamide

Product 1

HCID 116013222-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-ethylsulfamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The crude 2-(2,3 dihydrobenzo[1,4]dioxin-2-yl)ethylamine in dioxane (100 mL) was combined with sulfamide (3.0 g, 31 mmol) and heated to reflux for 2 h. The solution was cooled and evaporated in vacuo to yield an orange solid, which was purified by column chromatography (DCM:MeOH—10:1) to yield a white solid. The solid was re-crystallized from DCM to yield the title compound as a solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThe solution was cooled
  4. customevaporated in vacuo
  5. customto yield an orange solid, which
  6. customwas purified by column chromatography (DCM:MeOH—10:1)
  7. customto yield a white solid
  8. customThe solid was re-crystallized from DCM

Sources & evidence

ORD record
ord-f352078aff374c328060cb48faf4c0e9
Source dataset
uspto-grants-2014_10
Patent number
US08853263B2

Reaction notes

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