4-Isopropylaniline → 4-Isopropylphenyl cyanamide

HRID 977514

Reaction equation

HRID 977514 reaction equation
[N:1]#[C:2]Br.[CH:4]([C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)([CH3:6])[CH3:5]>C(OCC)C>[CH:4]([C:7]1[CH:13]=[CH:12][C:10]([NH:11][C:2]#[N:1])=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 74644-IsopropylanilineHCID 10476Cyanogen Bromide

Product 1

HCID 187831744-Isopropylphenyl cyanamideYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of cyanogen bromide (1.59 g, 15 mmol) in diethylether (20) was added dropwise to a solution of 4-isopropylaniline (3.24 g) in diethylether (50 mL) at 4° C. with stirring. After the addition, the reaction mixture was kept stirring at room temperature for 18 h. Then a solution with white precipitates formed and the precipitates were removed by filtration. The etherate solution was washed with aqueous HCl (1N, 30 mL, two times) as well as brine, dried over MgSO4, filtered, concentrated, and dried under vacuum to yield 4-isopropylphenyl cyanamide (2.0 g, 84%).

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was kept stirring at room temperature for 18 h
  3. customThen a solution with white precipitates
  4. customformed
  5. customthe precipitates were removed by filtration
  6. washThe etherate solution was washed with aqueous HCl (1N, 30 mL, two times) as well as brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customdried under vacuum

Sources & evidence

ORD record
ord-7c50511a83284124a206dc3d0b2dd08f
Source dataset
uspto-grants-1997_03
Patent number
US05614630

Linked notes

Loading…