N-Isopropylpropane-1,3-diamine → N-[3-(isopropylamino)propyl]-N'-(5-chloro-2-methylphenyl)urea hydrochloride

HRID 27842Notes

Reaction equation

HRID 27842 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Cl: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]>ClCCl>[ClH:8].[CH:12]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:10]([NH:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[CH3:1])=[O:11])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 76888N-Isopropylpropane-1,3-diamineHCID 27696325-Chloro-2-methylphenyl isocyanate

Product 1

HCID 20526049N-[3-(isopropylamino)propyl]-N'-(5-chloro-2-methylphenyl)urea hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 16.7 g. of 2-methyl-5-chlorophenylisocyanate and 50 ml. of dichloromethane was added to a stirred, cooled solution of 35 g. of N-isopropyl-1,3-diaminopropane and 250 ml. of dichloromethane. The temperature was kept at -5° to 0° C. during addition. Stirring was continued at room temperature for 20 minutes. The precipitated solid was separated by filtration. The filtrate 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, then extracted with dichloromethane. The dichloromethane solution was dried over magnesium sulfate, then evaporated to dryness. The residue was dissolved in ethanol and saturated with hydrogen chloride. The solution was evaporated to dryness in vacuo. The residue was triturated with ether until it solidified. The solid was recrystallized from EtOH/Et2O to obtain N-[3-(isopropylamino)propyl]-N'-(5-chloro-2-methylphenyl)urea hydrochloride, m.p. 180°-183° C.

Workup

  1. temperaturecooled solution of 35 g
  2. additionThe temperature was kept at -5° to 0° C. during addition
  3. customThe precipitated solid was separated by filtration
  4. extractionThe filtrate was extracted with water
  5. extractionThe acid extract
  6. extractionextracted with dichloromethane
  7. dry with materialThe dichloromethane solution was dried over magnesium sulfate
  8. customevaporated to dryness
  9. dissolutionThe residue was dissolved in ethanol and saturated with hydrogen chloride
  10. customThe solution was evaporated to dryness in vacuo
  11. customThe residue was triturated with ether until it
  12. customThe solid was recrystallized from EtOH/Et2O

Sources & evidence

ORD record
ord-5c47f241818b43ccbfbf009fa7869e50
Source dataset
uspto-grants-1980_09
Patent number
US04224242

Reaction notes

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