Hydrochloric Acid → HCID 66816757, compound

HRID 1754989Notes

Reaction equation

HRID 1754989 reaction equation
[O-]CC.[Na+].C([O:7][C:8](=O)[CH2:9][CH2:10][N:11]([C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([Br:22])=[C:17]([CH3:23])[CH:16]=1)[C:12]([NH2:14])=[O:13])C.Cl>C(O)C>[Br:22][C:18]1[C:19]([CH3:21])=[CH:20][C:15]([N:11]2[CH2:10][CH2:9][C:8](=[O:7])[NH:14][C:12]2=[O:13])=[CH:16][C:17]=1[CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 66817903HCID 66817903, compound

Product 1

HCID 66816757HCID 66816757, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of sodium ethoxide (15.7 mg, 0.033 mmol) in ethanol (0.1 ml) was added to a solution of 3-[1-(4-bromo-3,5-dimethyl-phenyl)-ureido]-propionic acid ethyl ester (11.4 mg, 0.033 mmol) in ethanol (0.9 ml), and the mixture was stirred at room temperature for 24 hours. The mixture was adjusted to pH 4 with 1 N hydrochloric acid and then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give 1-(4-bromo-3,5-dimethyl-phenyl)-dihydro-pyrimidine-2,4-dione (9.8 mg, 99%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-af9b8b5204df4e32b058bcdd1e20561c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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