Hydrochloric Acid → HCID 60979273, compound

HRID 219666Notes

Reaction equation

HRID 219666 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][S:10]([NH:13][CH:14]([CH3:16])[CH3:15])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].B.C1COCC1.Cl.[OH-].[Na+]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH2:9][S:10]([NH:13][CH:14]([CH3:16])[CH3:15])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 60754457HCID 60754457, compound

Product 1

HCID 60979273HCID 60979273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of C-(3-cyano-phenyl)-N-isopropyl-methanesulfonamide (0.5 g, 2.06 mmol) in THF (10 mL) is added a solution of BH3−THF in THF (1 M, 10.3 mL). The mixture is sealed and heated in a microwave reactor at 100° C. for 120 seconds. The mixture is poured into 1 M HCl (50 mL), basified with 3 M NaOH to pH ˜10, extracted with DCM, dried with Na2SO4, filtered, and concentrated in vacuo to afford C-(3-aminomethyl-phenyl)-N-isopropyl-methanesulfonamide, which is used directly in the next step without further purification.

Workup

  1. customThe mixture is sealed
  2. extractionextracted with DCM
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bf137f5e2654d1f971eb86b2cb8e349
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…