4-Aminophenol → 1-(Cyclopropylmethyl)-3-(4-hydroxyphenyl)urea

HRID 515269Notes

Reaction equation

HRID 515269 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](Cl)(=O)[O:10]C1C=CC([N+]([O-])=O)=CC=1.[CH:22]1([CH2:25][NH2:26])[CH2:24][CH2:23]1.C(N(CC)CC)C>ClCCl>[CH:22]1([CH2:25][NH:26][C:9]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[O:10])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 8471TriethylamineHCID 75646CyclopropanemethanamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 671944861-(Cyclopropylmethyl)-3-(4-hydroxyphenyl)ureaYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Aminophenol (18.33 mmol, 2 g) and 4-nitrophenyl carbonochloridate (18.33 mmol, 3.69 g) in dichloromethane (10 mL) were stirred at room temperature for 30 minutes. Cyclopropylmethanamine (36.7 mmol, 3.72 mL, 2.61 g) was added followed triethylamine (55.0 mmol, 7.66 mL, 5.56 g). The reaction was allowed to stir at room temperature overnight. The reaction mixture was diluted with dichloromethane/saturated sodium hydrogen carbonate solution and filtered through a hydrophobic frit. The organic layer was concentrated and the residue was purified by silica column chromatography (eluent: 2-8% methanol in dichloromethane) to give the title compound (1.4 g). MS (ESI) m/z 207.1 [M+H]+

Workup

  1. filtrationfiltered through a hydrophobic frit
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica column chromatography (eluent: 2-8% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3c9df233b5b944d19f2b4ce141daf84f
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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