Benzenemethanamine, N-butyl- → N-Benzyl-N-butyl-N'-(3-chlorophenyl)urea

HRID 1731834Notes

Reaction equation

HRID 1731834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:17])OC2C=CC=CC=2)[CH:5]=[CH:6][CH:7]=1.[CH2:18]([NH:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1.CCCCCC>[CH2:18]([N:25]([CH2:26][CH2:27][CH2:28][CH3:29])[C:9]([NH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:17])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 75467Benzenemethanamine, N-butyl-HCID 232110Phenyl hydrogen (3-chlorophenyl)carbonimidate

Product 1

HCID 13733049N-Benzyl-N-butyl-N'-(3-chlorophenyl)urea

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1.46 g of phenyl N-(3-chlorophenyl)carbamate in 15 ml of tetrahydrofuran was added to a solution of 1.92 g of N-benzyl-n-butylamine in 20 ml of tetrahydrofuran and the mixture stirred under reflux for 24 hours. The mixture was diluted with hexane and the precipitate collected by filtration. Recrystallization from pentane afforded 1-benzyl-1-(n-butyl)-3-(3-chlorophenyl)urea, m.p. 69°-70° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationthe precipitate collected by filtration
  3. customRecrystallization from pentane

Sources & evidence

ORD record
ord-b2531c9fc7a9451e8ef34dde53f31da5
Source dataset
uspto-grants-1986_11
Patent number
US04623662

Reaction notes

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