4-Bromoaniline → N-(3-cyanophenyl)-N'-(4-bromophenyl)urea

HRID 582579Notes

Reaction equation

HRID 582579 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.O1CCCC1>C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([Br:12])=[CH:14][CH:15]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 8028TetrahydrofuranHCID 27333153-Isocyanatobenzonitrile

Product 1

HCID 18630693N-(3-cyanophenyl)-N'-(4-bromophenyl)ureaYield 80.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3-cyanophenyl isocyanate (3.76 g, 26.1 mmol) and 4-bromoaniline (4.5 g, 26.1 mmol) in 1:1 tetrahydrofuran:chloroform (100 mL). After 72 h at ambient temperature, product was isolated by filtration, the filtrate was washed with cold chloroform and air dried to give 6.6 g of N-(3-cyanophenyl)-N'-(4-bromophenyl)urea (21 mmol).

Workup

  1. customproduct was isolated by filtration
  2. washthe filtrate was washed with cold chloroform and air
  3. customdried

Sources & evidence

ORD record
ord-32de74a5d24642b1a81946095109b54c
Source dataset
uspto-grants-1999_07
Patent number
US05925635

Reaction notes

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