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

HRID 359976Notes

Reaction equation

HRID 359976 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 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 hours
  2. filtrationthe precipitate collected by filtration
  3. customRecrystallization from pentane

Sources & evidence

ORD record
ord-134d467bc59046bfb4e5e9554afd3518
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

Loading…