1,2-Dibromoethane → HCID 69037708, compound

HRID 1453814Notes

Reaction equation

HRID 1453814 reaction equation
Br[CH2:2][CH2:3]Br.[OH:5][N:6]([CH:22]([CH3:24])[CH3:23])[C:7]([NH:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19])=[O:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH:22]([N:6]1[C:7](=[O:8])[N:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[C:18]([F:19])([F:20])[F:21])=[O:11])[CH2:3][CH2:2][O:5]1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86606739HCID 86606739, compound

Product 1

HCID 69037708HCID 69037708, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1,2-Dibromoethane (0.06 ml) was added to a suspension of 1-hydroxyl-1-isopropyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.20 g) and potassium carbonate (0.20 g) in N,N-dimethylformamide at 20° C., and stirred for 3 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on silica gel, eluting with n-hexane/ethyl acetate (2:1), to give 2-isopropyl-4-(4-trifluoromethyl-3-pyridylcarbonyl)-perhydro-1,2,4-oxadiazin-3-one (0.25 g, Compound U-3).

Workup

  1. dry with materialthe organic phase dried (magnesium sulfate)
  2. customevaporated
  3. customthe residue purified by column chromatography on silica gel
  4. washeluting with n-hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-4ee0e36706d248b4abe6cf33954e3efb
Source dataset
uspto-grants-2009_01
Patent number
US07476685B2

Reaction notes

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