m-Tolyl isocyanate → 1-(4-Ethynylphenyl)-3-(3-methylphenyl)urea

HRID 589895Notes

Reaction equation

HRID 589895 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[CH:2].[C:10]1([CH3:19])[CH:15]=[CH:14][CH:13]=[C:12]([N:16]=[C:17]=[O:18])[CH:11]=1>C1COCC1>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:17]([NH:16][C:12]2[CH:13]=[CH:14][CH:15]=[C:10]([CH3:19])[CH:11]=2)=[O:18])=[CH:5][CH:4]=1)#[CH:2]

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 37600254-Ethynylaniline

Product 1

HCID 1186384341-(4-Ethynylphenyl)-3-(3-methylphenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-ethynylaniline (1.308 g, 11.18 mmol, 1 eq) in anhydrous THF (20 mL) under nitrogen atmosphere at room temperature was added dropwise m-tolyl isocyanate (1.684 mL, 1.2 eq). The yellow reaction solution was stirred at room temperature for 3 hours. The reaction was then partitioned between EtOAc and aq NH4Cl. The organic layer was isolated, washed with saturated aq NaHCO3, brine, and dried with anhydrous sodium sulfate. The upper solvent layer was decanted and concentrated. The resulting solid residue was chromatographed initially with EtOAc-Hex from 1:100 to 1:4 and then continued with an eluent from dichloromethane to MeOH-DCM 1:10. The product fractions were collected, concentrated, and the white solid was triturated with EtOAc-Hex (2:1) at room temperature for 18 h. Upon filtration, 1-(4-ethynylphenyl)-3-(3-methylphenyl)urea was obtained as white solid in amount of 2.134 g.

Workup

  1. customThe reaction was then partitioned between EtOAc and aq NH4Cl
  2. customThe organic layer was isolated
  3. washwashed with saturated aq NaHCO3, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe upper solvent layer was decanted
  6. concentrationconcentrated
  7. customThe resulting solid residue was chromatographed initially with EtOAc-Hex from 1:100 to 1:4
  8. customThe product fractions were collected
  9. concentrationconcentrated
  10. customthe white solid was triturated with EtOAc-Hex (2:1) at room temperature for 18 h
  11. filtrationUpon filtration

Sources & evidence

ORD record
ord-6da0ca2092694da0949daba15f966a09
Source dataset
uspto-grants-2016_01
Patent number
US09233968B1

Reaction notes

Loading…