2-Aminofluorene → Urea, 1-(2-chloroethyl)-3-(fluoren-2-yl)-

HRID 260769Notes

Reaction equation

HRID 260769 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[Cl:15][CH2:16][CH2:17][N:18]=[C:19]=[O:20]>C(OCC)C>[Cl:15][CH2:16][CH2:17][NH:18][C:19](=[O:20])[NH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 15392-AminofluoreneHCID 160352-Chloroethyl isocyanate

Product 1

HCID 276671Urea, 1-(2-chloroethyl)-3-(fluoren-2-yl)-Yield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2 g of 2-aminofluorene in 125 mL of anhydrous ethyl ether is added dropwise 1.25 g of 2-chloroethyl isocyanate. This solution is stirred for 16 h at room temperature, cooled at -20° C., and filtered. A white solid separated and was recrystallized from ethanol (white flakes), yield 40%, mp 206°-208° C., IR (KBr pellet): 3300 (NH), 1730 (C=O, ester), and 1640 cm-1 (C=O, ureido); 1H NMR (DMSO-d6 : CDCl3): 8.08 ppm, 7.44 ppm, 7.35 ppm, 7.3 ppm, 7.27 ppm, 7.25 ppm, 7.16 ppm, 7.13 ppm, 7.02 ppm, 6.97 ppm, 6.96 ppm, 6.94 ppm, 6.93 ppm, 6.9 ppm, 6.87 ppm, 6.8 ppm, 3.5 ppm, 3.36 ppm, 3.33 ppm, 3.3 ppm, 3.25 ppm, 3.23 ppm, 3.2 ppm, 2.85 ppm.

Workup

  1. temperaturecooled at -20° C.
  2. filtrationfiltered
  3. customA white solid separated
  4. customwas recrystallized from ethanol (white flakes), yield 40%, mp 206°-208° C., IR (KBr pellet)

Sources & evidence

ORD record
ord-8d38575e91a144978d97ef7f58d72b01
Source dataset
uspto-grants-1996_06
Patent number
US05530026

Reaction notes

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