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Cesium carbonate → 2-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

HRID 1446096
Notes
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Reaction equation

HRID 1446096 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:22])([CH2:19][CH:20]=[CH2:21])[CH2:9][N:10]2[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[N:12]=[C:11]2Cl)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:19]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[O:22][C:11]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:10]2[CH2:9]1)[CH:20]=[CH2:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 579554882-(4-Bromo-phenyl)-1-(2-chloro-4-nitro-imidazol-1-yl)-pent-4-en-2-ol

Product 1

HCID 442424052-Allyl-2-(4-bromo-phenyl)-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of crude 2-(4-Bromo-phenyl)-1-(2-chloro-4-nitro-imidazol-1-yl)-pent-4-en-2-ol in DMF (48 mL) was added Cs2CO3 (2.84 g, 8.7 mmol) and stirred for 2 h at 50° C. The reaction mixture was cooled to rt, quenched with water, diluted with EtOAC and washed with brine and water. The organic layers were separated, dried (MgSO4) and concentrated. The concentrates were recrystallized with EuOAc to provide 270 mg of white solid. 1H NMR (400 MHz, DMSO-d) 68.11 (s, 1H), 7.64 (m, 2H), 7.38 (m, 2H), 5.80 (m, 2H), 5.12 (m, 2H), 4.62 (d, J=11.2 Hz, 1H), 4.01 (d, J=11.2 Hz, 1H), 2.96 (m, 2H); ESI MS m/z 352 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customquenched with water
  3. additiondiluted with EtOAC
  4. washwashed with brine and water
  5. customThe organic layers were separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe concentrates were recrystallized with EuOAc

Sources & evidence

ORD record
ord-dc51a1600e184fff89352452638e4872
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07666864B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes