4-Isopropylaniline → 4-Isopropylphenyl cyanamide

HRID 54464

Reaction equation

HRID 54464 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-d8ec55e141424ed1a7ead9eed3a444d6
Source dataset
uspto-grants-1997_04
Patent number
US05622968

Linked notes

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