Phenyl Isothiocyanate → HCID 2063437, compound

HRID 243517Notes

Reaction equation

HRID 243517 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH2:11][CH2:12][CH2:13][OH:14]>C1COCC1>[OH:14][CH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[S:9]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 90863-Amino-1-propanol

Product 1

HCID 2063437HCID 2063437, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenyl isothiocyanate (200 mg) in abs. THF (2 ml) was added dropwise under argon and with stirring to a solution of 3-amino-1-propanol (114.5 mg) in abs. THF (2 ml). The reaction mixture was stirred at room temperature for two hours. After removing the solvent, the residue was dissolved in aqueous HCl and washed with ether. Subsequently, the aqueous phase was basified with potassium carbonate and extracted three times with ether. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative chromatography, and the product-containing fractions were combined, freed of acetonitrile, basified and extracted three times with ethyl acetate. The organic phases were combined, dried (MgSO4) and filtered. After removing the solvent, 114 mg of the desired product were obtained.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in aqueous HCl
  3. washwashed with ether
  4. extractionextracted three times with ether
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative chromatography
  9. extractionextracted three times with ethyl acetate
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customAfter removing the solvent

Sources & evidence

ORD record
ord-58a2cce4dbc940eca1cc81169d557b57
Source dataset
uspto-grants-2014_02
Patent number
US08653259B2

Reaction notes

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