Benzoyl isothiocyanate → HCID 18474028, compound

HRID 2227476Notes

Reaction equation

HRID 2227476 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)([CH3:4])([CH3:3])[CH3:2].C([N:30]=[C:31]=[S:32])(=O)C1C=CC=CC=1>CC(C)=O>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][C:31]([NH2:30])=[S:32])[CH:12]=[CH:11][C:10]=1[N:16]1[CH:20]=[CH:19][CH:18]=[N:17]1)=[O:21])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 53803346HCID 53803346, compound

Product 1

HCID 18474028HCID 18474028, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of the compound (1.0 g) obtained in Example 2b and acetone (30 ml), benzoyl isothiocyanate (0.52 ml) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 10 minutes and then concentrated at reduced pressure. Methanol (50 ml) and potassium carbonate (0.53 g) were added to the resulting residue. The reaction mixture was stirred at room temperature for 80 minutes and then concentrated at reduced pressure. Water was added to the resulting residue and extraction with ethyl acetate was conducted. The organic layer was washed with brine, dried with anhydrous sodium sulfate and then concentrated at reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=3:1) to give the titled compound quantitatively.

Workup

  1. additionwas added dropwise at room temperature
  2. concentrationconcentrated at reduced pressure
  3. additionMethanol (50 ml) and potassium carbonate (0.53 g) were added to the resulting residue
  4. stirringThe reaction mixture was stirred at room temperature for 80 minutes
  5. concentrationconcentrated at reduced pressure
  6. additionWater was added to the resulting residue and extraction with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. concentrationconcentrated at reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane=3:1)

Sources & evidence

ORD record
ord-c21c79c054aa4d758b4b450471bb4072
Source dataset
uspto-grants-2002_07
Patent number
US06414005B1

Reaction notes

Loading…