Hydrochloric Acid → HCID 59218337, compound

HRID 2246406Notes

Reaction equation

HRID 2246406 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][C:6]([CH3:8])=O)[CH3:2].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][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][CH3:34])[C:13]=1[CH:14]=O.[NH2:35][C:36]([NH2:38])=[O:37].Cl>O1CCCC1>[CH2:1]([O:3][C:4]([C:5]1[CH:14]([C:13]2[C:16]([CH2:20][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][CH3:34])=[CH:17][CH:18]=[CH:19][C:12]=2[O:11][CH3:10])[NH:35][C:36](=[O:37])[NH:38][C:6]=1[CH3:8])=[O:9])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 8868Ethyl AcetoacetateHCID 85902263HCID 85902263, compound

Product 1

HCID 59218337HCID 59218337, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethylacetoacetate (1.13 g, 8.6 mmol), 2-methoxy-6-pentadecyl benzaldehyde (3 g, 8.6 mmol) and urea (1.04 g, 17.3 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 recrystallised 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. customrecrystallised from hexane

Sources & evidence

ORD record
ord-33fb8634dac441279a69ed30a386f76e
Source dataset
uspto-grants-2010_03
Patent number
US07687511B2

Reaction notes

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