Phenyl isocyanate → HCID 68467649, compound

HRID 502992Notes

Reaction equation

HRID 502992 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])=[N:5][N:4]=[C:3]1[C:14]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C.[C:29]1([N:35]=[C:36]=[O:37])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])=[N:5][N:4]=[C:3]1[C:14]1([NH:19][C:36]([NH:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:37])[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 68466643HCID 68466643, compound

Product 1

HCID 68467649HCID 68467649, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-[4-Methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]cyclopentanamine (263 mg) was dissolved in chloroform (5 ml) and then diisopropylethylamine (1.7 ml) and phenyl isocyanate (0.43 ml) were added thereto, followed by stirring at room temperature for 90 minutes. The reaction solution was diluted with a saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform (10 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting residue was purified by column chromatography (methanol:chloroform=1:19) and the resulting solid washed with ethyl acetate to obtain 68 mg of 1-{1-[4-methyl-5-(2-methylphenyl)-1,2,4-triazol-3-yl]cyclopentyl}-3-phenylurea (white solid).

Workup

  1. extractionfollowed by extraction with chloroform (10 ml×2)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customThe resulting residue was purified by column chromatography (methanol:chloroform=1:19)
  6. washthe resulting solid washed with ethyl acetate

Sources & evidence

ORD record
ord-0ff2108beb724294a5b0bf332cc97acf
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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