Urea → HCID 55263325, compound

HRID 1508889Notes

Reaction equation

HRID 1508889 reaction equation
Br[CH:2]([CH:8]=O)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[NH2:10][C:11]([NH2:13])=[O:12]>CN(C=O)C>[NH2:13][C:11]1[O:12][C:2]([CH2:3][C:4]([O:6][CH3:7])=[O:5])=[CH:8][N:10]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 13948279Methyl 3-bromo-4-oxobutanoate

Product 1

HCID 55263325HCID 55263325, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A 250-mL round bottom flask was charged with methyl 3-bromo-4-oxobutanoate (5.00 g, 25.6 mmol) and urea (2.08 g, 34.6 mmol) in DMF (15 mL) and heated to 110° C. for 30 minutes. After this time, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was absorbed onto silica and purified by chromatography on silica using dichloromethane/(89:9:1 dichloromethane/methane/conc. NH4OH) (10:0 to 0:10) as eluent, to afford the title compound (0.72 g, 18%) as a red oil. MW=156.14. 1H NMR (DMSO-d6, 300 MHz) δ 9.54 (s, 1H), 6.48 (s, 2H), 6.45 (s, 1H), 3.64 (s, 2H), 3.62 (s, 3H).

Workup

  1. temperatureAfter this time, the mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was absorbed onto silica
  4. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-20ade2cbdd074c969623690b928ddd77
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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