Hydrochloric Acid → 5-ethoxycarbonyl-4-(2-ethoxy-6-pentadecylphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

HRID 424861Notes

Reaction equation

HRID 424861 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([CH3:8])=O)[CH3:2].[CH2:10]([O:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:14]=1[CH:15]=O)[CH3:11].[NH2:36][C:37]([NH2:39])=[O:38].Cl>O1CCCC1>[CH2:1]([O:3][C:4]([C:5]1[CH:15]([C:14]2[C:17]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:18][CH:19]=[CH:20][C:13]=2[O:12][CH2:10][CH3:11])[NH:36][C:37](=[O:38])[NH:39][C:6]=1[CH3:8])=[O:9])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 8868Ethyl AcetoacetateHCID 225745702-Ethoxy-6-pentadecyl benzaldehyde

Product 1

HCID 104365325-ethoxycarbonyl-4-(2-ethoxy-6-pentadecylphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethylacetoacetate (1.25 g, 8.5 mmol), 2-ethoxy-6-pentadecyl benzaldehyde (3 g, 8.5 mmol) and urea (1.1 g, 17 mmol) in tetrahydrofuran (20 mL) was heated to reflux (65-70° C.) in the presence of hydrochloric acid (30%) for 7 h. The reaction mixture after being cooled to room temperature was poured into crushed ice (20 g) and stirred for 5 min. The viscous liquid was extracted with ethylacetate (40 mL) and was washed with 1N hydrochloric acid, water, sodium bicarbonate and brine. After drying over anhydrous sodium sulfate, the solvent was evaporated to yield light yellow oil. This crude product was purified by flash column chromatography and recrystallized from hexane to get white crystalline solid of title compound.

Workup

  1. additionwas poured
  2. extractionThe viscous liquid was extracted with ethylacetate (40 mL)
  3. washwas washed with 1N hydrochloric acid, water, sodium bicarbonate and brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customto yield light yellow oil
  7. customThis crude product was purified by flash column chromatography
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-9050021978d944ab8e7b8852d53edba8
Source dataset
uspto-grants-2012_01
Patent number
US08106062B1

Reaction notes

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