Triethylamine → 3-(5-(Cyclopent-1-en-1-yl)-2-nitrophenyl)-1-methyl-1-propylurea
Reaction equation
[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([CH:12]=2)[NH2:11])[CH2:5][CH2:4][CH2:3][CH:2]=1.C(N(CC)CC)C.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[CH3:35][NH:36][CH2:37][CH2:38][CH3:39]>ClCCl>[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([NH:11][C:27](=[O:33])[N:36]([CH3:35])[CH2:37][CH2:38][CH3:39])[CH:12]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1Participants
Procedure
To a solution of 5-(cyclopent-1-en-1-yl)-2-nitroaniline (0.13 g, 0.61 mmol, 1.0 equiv.) in dichloromethane were added triethylamine (0.68 mL, 4.90 mmol, 8.0 equiv.) and triphosgene (0.18 g, 0.61 mmol, 1.0 equiv.) at 0° C. The mixture was warmed to room temperature and stirred for 3 h at room temperature. Triethylamine (0.17 mL, 1.22 mmol, 2.0 equiv.) and N-methylpropan-1-amine (0.07 g, 0.92 mmol, 1.5 equiv.) were added slowly to the reaction mixture. The reaction mixture was slowly warmed to 50° C. and stirred for 2 h. The mixture was diluted with dichloromethane, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give crude 3-(5-(cyclopent-1-en-1-yl)-2-nitrophenyl)-1-methyl-1-propylurea (0.14 g, 76% crude yield) which was used in the next step without further purification.
Workup
- temperatureThe reaction mixture was slowly warmed to 50° C.
- stirringstirred for 2 h
- washwashed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9011f254bfa148c4a591a6fd24416f56
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447030B2
Reaction notes
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