Hydrochloric Acid → HCID 86251909, compound

HRID 1710816Notes

Reaction equation

HRID 1710816 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=1[C:12](=O)[CH3:13].[S-:15][C:16]#[N:17].[K+].Cl>C(O)C.O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[NH:3][C:16](=[S:15])[NH:17][CH:12]2[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516872Potassium thiocyanateHCID 4311764Sodium borohydrideHCID 136911411-(2-Amino-3-methoxyphenyl)ethan-1-one

Product 1

HCID 86251909HCID 86251909, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
65 °C

Procedure

Under an atmosphere of nitrogen and at a temperature of 65° C., sodium borohydride (154 mg, 4 mmol) was added to a solution of 1-(2-amino-3-methoxy-phenyl)-ethanone (960 mg, 6 mmol) in ethanol (8 ml). After stirring at 65° C. overnight, water (5 ml), a solution of potassium thiocyanate (620 mg, 6 mmol) in water (3 ml), and a solution of conc. HCl (3 ml) in water (4 ml) were added subsequently. The mixture was then stirred for an additional 3 h at 65° C. Upon cooling, the solvent was evaporated and the residue was taken up in water/ethyl acetate. The organic phase was dried (Na2SO4), and the solvent was evaporated. Chromatography (silica gel, heptan/ethyl acetate=100/0-70/30) gave the title compound (700 mg, 58%).

Workup

  1. stirringThe mixture was then stirred for an additional 3 h at 65° C
  2. temperatureUpon cooling
  3. customthe solvent was evaporated
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cb6a2b2fbc784f72bc06d1770b8b9ec0
Source dataset
uspto-grants-2010_09
Patent number
US07790733B2

Reaction notes

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