2,5-Dichloroaniline → 2,5-Dichlorophenylcyanamide

HRID 1858983Notes

Reaction equation

HRID 1858983 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].Br[C:11]#[N:12]>O>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH:4][C:11]#[N:12]

Participants

4

Reactant 2

HCID 72622,5-DichloroanilineHCID 10476Cyanogen Bromide

Product 1

HCID 107027292,5-DichlorophenylcyanamideYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a heterogeneous slurry of 2,5-dichloroaniline (3.0 g, 18.5 mmol) in 60 mL of water at 4° C. was added solid BrCN (1.22 g, 11.3 mmol) slowly. After 5 minutes the cooling bath was removed and the heterogeneous reaction mixture was stirred at room temperature for 24 hours to yield the product in water suspension. The product was collected by filtration, washed with water (100 mL), and dried under vacuum to yield the pure product (2 g, 60% yield).

Workup

  1. customAfter 5 minutes the cooling bath was removed
  2. customto yield the product in water suspension
  3. filtrationThe product was collected by filtration
  4. washwashed with water (100 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5de3b2cf1d1f4f31bbcd6e226d08c622
Source dataset
uspto-grants-2000_11
Patent number
US06153604

Reaction notes

Loading…