Urea → HCID 82973661, compound

HRID 1524051Notes

Reaction equation

HRID 1524051 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:6]=1[F:12])=O.[NH2:13][C:14]([NH2:16])=[O:15].[OH-].[Na+]>CC#N>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:13]=[C:14]([NH2:16])[O:15][CH:2]=2)=[C:6]([F:12])[CH:7]=1

Participants

5

Reactant 3

HCID 1176UreaHCID 14798Sodium HydroxideHCID 221214832-Bromo-1-(4-bromo-2-fluorophenyl)ethanone

Product 1

HCID 82973661HCID 82973661, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-bromo-1-(4-bromo-2-fluorophenyl)ethanone (53 mg, 0.18 mmol) and urea (10.6 mg, 0.18 mmol) in CH3CN (0.7 mL) was heated at 80° Celsius for 18 hours. The mixture was cooled to rt and made basic with NaOH (2 N). The resulting solution was extracted with EtOAc and the extract was dried (Na2SO4), filtered, and concentrated to dryness. The residue was purified using FCC to give 4-(4-bromo-2-fluorophenyl)oxazol-2-amine (37 mg, 82%). MS (ESI): mass calcd. for C9H6BrFN2O, 255.96; m/z found, 257.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 7.78 (m, 1H), 7.58 (d, J=4.3, 1H), 7.36-7.32 (m, 1H), 7.28 (dd, J=10.5, 1.9, 1H), 4.60 (s, 2H).

Workup

  1. extractionThe resulting solution was extracted with EtOAc
  2. dry with materialthe extract was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified

Sources & evidence

ORD record
ord-da778655b2ec41a080199a3be053d1e7
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…