Sulfamic Acid → HCID 57443657, compound

HRID 660402Notes

Reaction equation

HRID 660402 reaction equation
[CH2:1]=[C:2]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.B.C1COCC1.[NH2:19]S(O)(=O)=O.[OH-].[Na+]>C1COCC1>[O:4]1[CH2:3][CH:2]([CH2:1][NH2:19])[CH2:8][O:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]1=2

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 14798Sodium HydroxideHCID 5954503-Methylene-3,4-dihydro-2H-1,5-benzodioxepinHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 57443657HCID 57443657, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepine (5.00 g, 30.8 mmol) was dissolved in dry THF (100 mL). Borane-THF (1.0 M in THF, 10.3 mL) was added at 0° C. The reaction was stirred at RT for 5 hours. Aminosulfonic acid (6.97 g, 61.6 mmol) was added. The reaction was heated to reflux overnight. The reaction was cooled to room temperature and aqueous sodium hydroxide (3.0 M, 100 mL) was added. The solution was extracted with ethyl acetate (3×100 mL). The combined organic solution was dried over MgSO4. The solution was concentrated under vacuum and purified by chromatography (2% to 8% methanol in dichloromethane) to yield ((3,4-dihydro-2H-benzo[b][1,4]dioxepin-3-yl)methyl)amine as a colorless oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. temperatureThe reaction was cooled to room temperature
  4. extractionThe solution was extracted with ethyl acetate (3×100 mL)
  5. dry with materialThe combined organic solution was dried over MgSO4
  6. concentrationThe solution was concentrated under vacuum
  7. custompurified by chromatography (2% to 8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0d847b1147f24373901713dc66032e3a
Source dataset
uspto-grants-2011_12
Patent number
US08084490B2

Reaction notes

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