Dichloromethane → N-[3-(isopropylamino)propyl]-N'-(2,5-dimethylphenyl)urea, hydrochloride
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].[CH:12]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])([CH3:14])[CH3:13].[Cl:20]CCl>>[ClH:20].[CH:12]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:10]([NH:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])=[O:11])([CH3:14])[CH3:13]Participants
Procedure
A solution of 14.7 grams of 2,5-dimethylphenylisocyanate and 50 ml. of dichloromethane was added to a stirred, cooled solution of 35 g. N-isopropyl-1,3-diaminopropane and 400 ml. of dichloromethane. The temperature was kept between -5° and 0° C. during addition. Stirring was continued at room temperature for one hour. The solution was extracted with water, then with 200 ml. of 15% hydrochloric acid (v/v). The acid extract was made basic with saturated sodium carbonate solution and extracted with dichloromethane. The dichloromethane solution was dried over magnesium sulfate, then evaporated to dryness. The residue was dissolved in ether and saturated with hydrogen chloride. The solid was separated and recrystallized from EtOH/Et2O to obtain N-[3-(isopropylamino)propyl]-N'-(2,5-dimethylphenyl)urea, hydrochloride, m.p. 152°-154° C.
Workup
- temperaturecooled solution of 35 g
- additionThe temperature was kept between -5° and 0° C. during addition
- extractionThe solution was extracted with water
- extractionThe acid extract
- extractionextracted with dichloromethane
- dry with materialThe dichloromethane solution was dried over magnesium sulfate
- customevaporated to dryness
- dissolutionThe residue was dissolved in ether and saturated with hydrogen chloride
- customThe solid was separated
- customrecrystallized from EtOH/Et2O
Sources & evidence
- ORD record
- ord-eb426d8c8d394d5a833828563dad3c96
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04224242
Reaction notes
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