Phenylurea → HCID 58081167, compound

HRID 928405Notes

Reaction equation

HRID 928405 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:12][C:13](=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C=O)C>[C:1]1([NH:7][C:8]2[O:9][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6145PhenylureaHCID 66144Ethyl bromopyruvate

Product 1

HCID 58081167HCID 58081167, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-phenylurea (2.0 g, 14.69 mmol) and ethyl 3-bromo-2-oxopropanoate (2.16 ml, 14.69 mmol) in DMF (58 ml) was heated at 60° C. for 3 hours. The reaction mixture was allowed to cool to rt and quenched with water (300 ml)/Na2CO3-solution (50 ml). The product was extracted with EA (2×). The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure to afford crude product. Purification by flash-chromatography (Silica gel 62 g, gradient: cyclohexane/EA (80 ml/min.) from 95/5 (5 min.) to 80/20 (25 min.)) afforded the title compound. HPLC (Method U): RtU=1.91 min, MS (Method D) [M+H]+=233.1.

Workup

  1. customquenched with water (300 ml)/Na2CO3-solution (50 ml)
  2. extractionThe product was extracted with EA (2×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto afford crude product
  8. customPurification by flash-chromatography (Silica gel 62 g, gradient: cyclohexane/EA (80 ml/min.) from 95/5 (5 min.) to 80/20 (25 min.))

Sources & evidence

ORD record
ord-ef10e2a08b654daba0cb8a599abf61c5
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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