Ethanol → HCID 16112965, compound

HRID 2240926Notes

Reaction equation

HRID 2240926 reaction equation
[F:1][CH:2]([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](O)C=2)=O)=[CH:6][CH:5]=1.Cl.[CH3:23][NH:24][C:25]([NH2:27])=[NH:26].[C:28](=[O:31])([O-])[O-].[Na+].[Na+].C([OH:36])C>>[NH2:26][C:25]1[N:24]([CH3:23])[C:28](=[O:31])[C:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:1])[F:21])=[CH:9][CH:8]=2)([C:11]2[CH:13]=[CH:18][CH:17]=[C:16]([OH:36])[CH:15]=2)[N:27]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 59790334HCID 59790334, compoundHCID 178485118HCID 178485118, compound

Product 1

HCID 16112965HCID 16112965, compoundYield 64%

Conditions

Temperature
85 °C

Procedure

1-(4-(difluoromethoxy)phenyl)-2-(3-hydroxyphenyl)ethane-1,2-dione (0.11 g, 0.38 mmol) was dissolved in ethanol (5 mL). Methylguanidine hydrochloride (0.052 g, 0.47 mmol) was added followed by sodium carbonate (0.050 g, 0.47 mmol). The mixture was stirred at 85° C. overnight 15 hours. The solvent was removed and the material is absorbed onto celite. Purification by flash chromatography afforded 2-amino-4-(4-(difluoromethoxy)phenyl)-4-(3-hydroxyphenyl)-1-methyl-1H-imidazol-5(4H)-one (0.085 g, 64%).

Workup

  1. customThe solvent was removed
  2. customthe material is absorbed onto celite
  3. customPurification by flash chromatography

Sources & evidence

ORD record
ord-b977d5e6c5ba49fbbd2421b3273dbf91
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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