Hydrochloric Acid → 2-(Isopropylsulfonyl)ethanamine

HRID 915301

Reaction equation

HRID 915301 reaction equation
[CH:1]([S:4]([CH2:7][C:8]#[N:9])(=[O:6])=[O:5])([CH3:3])[CH3:2].CSC.B.Cl>C1COCC1>[CH:1]([S:4]([CH2:7][CH2:8][NH2:9])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27785302-(Isopropylsulfonyl)acetonitrileHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 220177492-(Isopropylsulfonyl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to Procedure K. 2-iso-Propylsulfonylacetonitrile (0.50 g, 3.39 mmol) was dissolved in THF and warmed to reflux under N2. Borane dimethylsulfide (2M, 1.7 mL, 3.39 mmol) was added dropwise and the reaction was stirred for an additional 40 minutes at reflux. After cooling the reaction to rt, HCl (2 M in MeOH) was added to the reaction slowly due to gas evolution. The volatiles were removed and fresh methanol was added to the resulting residue. Again, the volatiles were removed and the resulting residue was taken up in CH2Cl2 (25 mL) and washed with saturated potassium carbonate (aqueous). The organic layer was dried over sodium sulfate and the volatiles were removed to afford the title compound. GC-MS m/z 152 (MH+).

Workup

  1. customPrepared
  2. temperaturewarmed
  3. temperatureto reflux under N2
  4. temperatureat reflux
  5. temperatureAfter cooling
  6. customthe reaction to rt
  7. customThe volatiles were removed
  8. additionfresh methanol was added to the resulting residue
  9. customAgain, the volatiles were removed
  10. washwashed with saturated potassium carbonate (aqueous)
  11. dry with materialThe organic layer was dried over sodium sulfate
  12. customthe volatiles were removed

Sources & evidence

ORD record
ord-05a545cc9d524d9f87df1cbe1871796c
Source dataset
uspto-grants-2007_09
Patent number
US07265123B2

Linked notes

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