Pyridine → 1-Tert-butyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea
Reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:8]1[C:16]2[C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[NH2:21].N1C=CC=CC=1>O1CCCC1>[C:1]([NH:5][C:6]([NH:21][C:9]1[CH:10]=[CH:11][C:12]2[O:13][C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=3[C:16]=2[CH:8]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
tert-Butylisocyanate (0.55 g, 5.5 mmol) was added to a cooled (0° C.) solution of 6,7,8,9-tetrahydro-dibenzofuran-2-ylamine (0.94 g, 5.0 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred for 10 minutes at 0° C. and then allowed to warm to ambient temperature for 5 hours. An additional portion of tert-butylisocyanate (0.65 mL) was added the reaction mixture was stirred overnight. The reaction was incomplete, so pyridine (10 mL) was added and the reaction mixture was heated to reflux for 4.5 hours and then concentrated under reduced pressure. The crude material was dissolved in ethyl acetate and washed with 1 N HCl, water, and brine, dried (Na2SO4) and concentrated. The crude material was recrystallized from acetonitrile to provide 1-tert-butyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea (0.71 g). Mp 310-312° C. (DEC); Anal. Calcd. for C17H22N2O2: C, 71.30; H, 7.74; N, 9.78; Found: C, 71.18; H, 7.84; N, 9.79.
Workup
- temperatureto warm to ambient temperature for 5 hours
- stirringwas stirred overnight
- temperaturethe reaction mixture was heated
- temperatureto reflux for 4.5 hours
- concentrationconcentrated under reduced pressure
- dissolutionThe crude material was dissolved in ethyl acetate
- washwashed with 1 N HCl, water, and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customThe crude material was recrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-06ff6d1d31a64478836532d68357153d
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601856B2
Reaction notes
Loading…