Cyanogen Bromide → 2-Chloro-5-ethylphenylcyanamide

HRID 1858986Notes

Reaction equation

HRID 1858986 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][C:3]=1[NH2:4].Br[C:12]#[N:13]>O>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][C:3]=1[NH:4][C:12]#[N:13]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 124650462-Chloro-5-ethylaniline

Product 1

HCID 105593012-Chloro-5-ethylphenylcyanamideYield 100.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a heterogeneous slurry of 2-chloro-5-ethylaniline (1.6 g, 10 mmol) in 60 mL of water at 4° C. was added solid BrCN (0.848 g, 8 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 precipitates were collected by filtration, washed with water (100 mL), and dried under vacuum to yield the pure title compound (1.45 g, 80% yield).

Workup

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

Sources & evidence

ORD record
ord-63774565f3e0431f925976ea2cb9b52a
Source dataset
uspto-grants-2000_11
Patent number
US06153604

Reaction notes

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