4-Fluorophenyl isocyanate → N-(2-methylcarbamoyl-5-tert-butylfuryl)-N'-(4-fluorophenyl)urea

HRID 1698910Notes

Reaction equation

HRID 1698910 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10])=[O:4].[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH:10][C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=1)=[O:24])=[O:4]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 18322380N-methyl-3-amino-5-tert-butyl-2-furancarboxamide

Product 1

HCID 9923703N-(2-methylcarbamoyl-5-tert-butylfuryl)-N'-(4-fluorophenyl)ureaYield 63.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-methyl-3-amino-5-tert-butylfuran-2-carboxamide (0.15 g, 0.76 mmol) in anh. toluene (2 mL) at the reflux temp. was slowly added 4-fluorophenyl isocyanate (0.10 g, 0.76 mmol, 1.0 equiv). The resulting solution was allowed to stir at the reflux temp. for 14 h, cooled to room temp., and concentrated under reduced pressure. The residue was purified by flash chromatography (15 g SiO2, gradient from 50% CH2Cl2/hexane to 100% CH2Cl2, then to 20% EtOAc/CH2Cl2) to afford N-(2-methylcarbamoyl-5-tert-butylfuryl)-N′-(4-fluorophenyl)urea (0.16 g, 61%): mp 109-11° C., TLC (30% EtOAc/CH2Cl2) Rf0.21; 1H NMR (CDCl3) δ1.29 (s, 9H), 2.89 (d, J=4.8 Hz, 3H), 6.02 (br q, J=4.8 Hz, 1H), 6.98 (app td, J=16.6, 4.1 Hz, 2H), 7.01 (s, 1H), 7.34-7.39 (m, 2H), 8.05 (br s, 1H), 9.14 (s, 1H); 13C NMR (CDCl3) δ25.5, 28.7 (3C), 33.1, 100.7, 115.6 (d, JC-F=23.2 Hz, 2C), 121.5 (d, JC-F=7.3 Hz, 2C), 128.3, 134.5 (br s), 152.4, 158.9 (d, JC-F=242.9 Hz, 1C), 161.6, 165.8; FAB-LRMS m/z (rel abundance) 334 (M+H, 100%).

Workup

  1. temperaturecooled to room temp.
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (15 g SiO2, gradient from 50% CH2Cl2/hexane to 100% CH2Cl2

Sources & evidence

ORD record
ord-ce74755e9c98424e814374a84940b3fe
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

Loading…