4-Isopropylaniline → 4-Isopropylphenyl cyanamide

HRID 356684

Reaction equation

HRID 356684 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-5a383a1038184c43a005921c81d5fccb
Source dataset
uspto-grants-1998_11
Patent number
US05837737

Linked notes

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