Dihydroxyacetone → HCID 178519857, compound

HRID 1823948Notes

Reaction equation

HRID 1823948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[NH:10])[NH2:9].[OH:11][CH2:12][C:13]([CH2:15]O)=O.[Cl-].[NH4+]>[OH-].[NH4+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][CH:15]=[C:13]([CH2:12][OH:11])[N:10]=1

Participants

5

Reactant 3

HCID 670DihydroxyacetoneHCID 25517Ammonium ChlorideHCID 27409182-Chlorobenzimidamide

Product 1

HCID 178519857HCID 178519857, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

According to literature reference (Huang, Y.; Luedtke, R. R.; Freeman, R. A.; Wu, L.; Mach, R. H. Bioorg. Med. Chem. 2001, 9, 3113–3122), to a mixture of 2-chlorobenzenecarboximidamide (5.4 g, 34.8 mmol), 1,3-dihydroxyacetone dimmer (6.2 g, 34.8 mmol) and ammonium chloride (7.5 g, 139 mmol) is added concentrated ammonium hydroxide (40 mL). The reaction mixture is then heated to reflux for 30 minutes after which time it is cooled to room temperature and poured into a ice/water mixture. This aqueous suspension is extracted with CH2Cl2 and the combined organic extracts are dried over sodium sulfate and concentrated to provide a crude solid. The crude product is recrystallized from ethyl acetate to afford 3.9 g of [2-(2-chlorophenyl)-1H-imidazol-4-yl]methanol.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux for 30 minutes after which time it
  3. extractionThis aqueous suspension is extracted with CH2Cl2
  4. dry with materialthe combined organic extracts are dried over sodium sulfate
  5. concentrationconcentrated
  6. customto provide a crude solid
  7. customThe crude product is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-60e11f0dc90146d3be0f55d2f9d4c108
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

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