Hydrochloric Acid → HCID 178442370, compound

HRID 2364912Notes

Reaction equation

HRID 2364912 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](=O)[CH2:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[NH2:18][C:19]([NH2:21])=[O:20].Cl.O>C(O)C.C(OCC)(=O)C>[CH2:6]([C:7]1[CH:8]=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:21]=[C:19]([OH:20])[N:18]=1)[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1176UreaHCID 11356889HCID 11356889, compound

Product 1

HCID 178442370HCID 178442370, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pentadecane-7,9-dione (60.0 g, 250 mmol) and 30 g (500 mmol) of urea were dissolved in 3750 mL of ethanol, and under a nitrogen atmosphere, 75 mL of concentrated hydrochloric acid was added, and the mixture was gradually heated until reflux, and allowed to reflux for 18.5 hours. After cooling down to room temperature, water and ethyl acetate were added, the oil phase was extracted, and washed with a saturated sodium bicarbonate solution and saturated saline in this order, and dried over magnesium sulfate and concentrated. The resultant concentrate was purified by a silica gel column (hexane•ethyl acetate) to obtain 31.2 g of 4,6-dihexylpyrimidin-2-ol.

Workup

  1. temperaturethe mixture was gradually heated
  2. temperatureuntil reflux
  3. temperatureto reflux for 18.5 hours
  4. extractionthe oil phase was extracted
  5. washwashed with a saturated sodium bicarbonate solution and saturated saline in this order
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. concentrationThe resultant concentrate
  9. customwas purified by a silica gel column (hexane•ethyl acetate)

Sources & evidence

ORD record
ord-4d739855a4e0492a9e5c5fd0992db4df
Source dataset
uspto-grants-2014_04
Patent number
US08697256B2

Reaction notes

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