Diethyl Ether → N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-N'-(4-chlorophenyl)urea

HRID 1904223Notes

Reaction equation

HRID 1904223 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][CH2:12][CH2:13][N:14]1[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]1[CH3:20].C(OCC)C>O1CCCC1>[CH3:20][C:15]1[N:14]([CH2:13][CH2:12][NH:11][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[C:18]([CH3:19])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 76934-Chlorophenyl IsocyanateHCID 137700502-(2,5-Dimethyl-1H-pyrrol-1-yl)ethan-1-amine

Product 1

HCID 13770055N-(2-(2,5-Dimethyl-1-pyrrolyl)ethyl)-N'-(4-chlorophenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

7.7 g (0.05 mol) of 4-chlorophenyl isocyanate, dissolved in 10 ml of tetrahydrofura, are added dropwise, over the coruse of 30 minutes, to 6.9 g (0.05 mol) of 1-(2-aminoethyl)-2,5-dimethylpyrrole, dissolved in 10 ml of tetrahydrofuran, a 20° C. The mixture is then left to stir at 20° C. for 60 minutes. After addition of diethyl ether to the reaction mixture the product crystallizes out, and is filtered off with suction and recrystallized from isopropanol. Yield: 8.4 g (58% of theory), Melting point: 175°-177° C. Elemental analysis: C15H18ClN3 0 (291.83) calculated: C 61.7 H 6.2 CL 12.2 N 14.4 0 5.5 found: C 61.0 H 6.5 Cl 12.5 N 14.6 0 5.8

Workup

  1. waitThe mixture is then left
  2. customcrystallizes out
  3. filtrationis filtered off with suction
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-26e96d5ac61e4eee9b8a525ffb4a0c0f
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

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