Guanidine Hydrochloride → HCID 12149476, compound

HRID 1816297Notes

Reaction equation

HRID 1816297 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])=O.Cl.[NH2:18][C:19]([NH2:21])=[NH:20].[OH-].[Na+]>C(O)C>[N+:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]1[CH:4]=[CH:3][N:18]=[C:19]([NH2:21])[N:20]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 14798Sodium HydroxideHCID 292656HCID 292656, compound

Product 1

HCID 12149476HCID 12149476, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(dimethylamino)2′-nitroacrylophenone (1.0 g, 4.54 mmol) in absolute ethanol (25 mL) was treated with guanidine hydrochloride (540 mg, 5.68 mmol), and 10N sodium hydroxide (200 μL). The reaction was heated to reflux for 18 hours. Upon cooling a white precipitate was collected by filtration and rinsed with diethyl ether to give 4-(2-nitrophenyl)-2-pyrimidineamine (400 mg). Additional material was obtained by concentration and chromatography on silica, eluting with 1;1 hexane:ethyl acetate.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 18 hours
  3. temperatureUpon cooling a white precipitate
  4. filtrationwas collected by filtration
  5. washrinsed with diethyl ether

Sources & evidence

ORD record
ord-bb185efd239f458f99844c540f839d45
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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