Sodium Cyanate → 1-Isopropyl-1-(4-methoxy-phenyl)-urea

HRID 445150Notes

Reaction equation

HRID 445150 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[O-:13][C:14]#[N:15].[Na+]>C(O)(=O)C>[CH:1]([N:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:14]([NH2:15])=[O:13])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 517096Sodium CyanateHCID 27594984-methoxy-N-(propan-2-yl)aniline

Product 1

HCID 130988041-Isopropyl-1-(4-methoxy-phenyl)-urea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 4.47 g (27.1 mmol) isopropyl-(4-methoxy-phenyl)-amine in 70 ml acetic acid are added in small portions 1.72 g (25.4 mmol) sodium cyanate while keeping the temperature below 15° C. by means of an ice bath. After stirring for 2 h at room temperature the acetic acid is evaporated and the residue is taken up in dichloromethane and washed with aqueous sodium hydroxide solution (1M). The organic phase is evaporated and the crude product is purified by recrystallization from dichloromethane/hexanes to yield 1-isopropyl-1-(4-methoxy-phenyl)-urea.

Workup

  1. customthe temperature below 15° C.
  2. customis evaporated
  3. washwashed with aqueous sodium hydroxide solution (1M)
  4. customThe organic phase is evaporated
  5. customthe crude product is purified by recrystallization from dichloromethane/hexanes

Sources & evidence

ORD record
ord-48fca9add93343c28be773acf4447825
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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