Phenyl isocyanate → HCID 10343646, compound

HRID 1085597Notes

Reaction equation

HRID 1085597 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:6]1=2.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:24]1([NH:30][C:31](=[O:32])[NH:1][CH2:2][CH2:3][S:4][CH:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[CH2:9][O:8][C:7]3[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:6]2=3)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 14724118HCID 14724118, compound

Product 1

HCID 10343646HCID 10343646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound f, 2.0 g, obtained in Reference Example 6 was dissolved in 100 ml of methylene chloride and 0.7 ml of phenyl isocyanate was added to the solution. The mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure. The residue was extracted with 200 ml of ethyl acetate. The extract was washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=2:1) to give 2.2 g of the desired compound.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. extractionThe residue was extracted with 200 ml of ethyl acetate
  3. washThe extract was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-66ae0ea0804649a1ae37d56dfd0bd5f7
Source dataset
uspto-grants-1991_04
Patent number
US05010104

Reaction notes

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