N-bromobutanimide → HCID 67212702, compound

HRID 1671346Notes

Reaction equation

HRID 1671346 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[CH:15]=[C:11]2[O:12][C:13]=1[CH3:14].C1C(=O)N([Br:26])C(=O)C1>CN(C=O)C>[Br:26][C:15]1[C:16]([CH3:18])=[N:17][N:10]2[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[C:13]([CH3:14])[O:12][C:11]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 591860073-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole

Product 1

HCID 67212702HCID 67212702, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole (Intermediate HE) (0.755 g, 2.69 mmol) in DMF (10 ml) is added NBS (0.502 g, 2.82 mmol). The reaction is stirred at RT for 30 mins and then partitioned between Na2CO3 and EtOAc. The mixture is extracted with EtOAc (×2) and the combined organic phases are dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. This resulting solid is recrystallised from hot EtOAc/iso-hexane to yield the title compound. MS: m/z 360.99 [M+H]+

Workup

  1. custompartitioned between Na2CO3 and EtOAc
  2. extractionThe mixture is extracted with EtOAc (×2)
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customThis resulting solid is recrystallised from hot EtOAc/iso-hexane

Sources & evidence

ORD record
ord-afff5bd28cc7413784a6fd549866e190
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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