Sodium Hydroxide → HCID 9838035, compound

HRID 2105259Notes

Reaction equation

HRID 2105259 reaction equation
[O:1]([C:3]#[N:4])[K].[N:5]1([CH:10]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH:11]([CH3:13])[CH3:12])[CH:9]=[CH:8][N:7]=[CH:6]1.[OH-].[Na+]>O.C(O)(=O)C>[N:5]1([CH:10]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:3]([NH2:4])=[O:1])=[CH:18][CH:19]=2)[CH:11]([CH3:13])[CH3:12])[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 22335511HCID 22335511, compoundHCID 178418250HCID 178418250, compound

Product 1

HCID 9838035HCID 9838035, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of KOCN (2.25 g) in water was added dropwise at RT to a mixture of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]benzenamine (0.0278 mol) in acetic acid (4 ml) and water (50 ml) and the mixture was stirred at RT for 1 hour. The mixture was neutralized with NaOH 3N and extracted with CH2Cl2 and CH3OH. The organic layer was washed with water, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.3). The pure fractions were collected and evaporated. The residue was recrystallized from 2-propanone, yielding 2.7 g (51.4%) (±)-4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenylurea (compound 266).

Workup

  1. extractionextracted with CH2Cl2 and CH3OH
  2. washThe organic layer was washed with water
  3. customdried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.3)
  7. customThe pure fractions were collected
  8. customevaporated
  9. customThe residue was recrystallized from 2-propanone

Sources & evidence

ORD record
ord-a4119b73bdf940d786326587deef44c4
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

Loading…