N-bromobutanimide → HCID 86655151, compound

HRID 69399Notes

Reaction equation

HRID 69399 reaction equation
[CH2:1]([NH:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:28][OH:29])[CH:14]=[C:15]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])=[CH:9][C:8]=1[CH3:30])[CH2:2][CH2:3][CH3:4].[Br:32]N1C(=O)CCC1=O>CN(C)C=O>[Br:32][CH:14]1[C:15]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)([C:16]([F:18])([F:17])[F:19])[O:29][N:28]=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])=[O:31])=[C:8]([CH3:30])[CH:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 76765796HCID 76765796, compound

Product 1

HCID 86655151HCID 86655151, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Butyl-4-[3-(3,5-dichloro-phenyl)-4,4,4-trifluoro-1-hydroxyimino-but-2-enyl]-2-methyl-benzamide (Example 3.1) (380 mg, 0.94 mmol) and N-bromosuccinimide (200 mg, 1.12 mmol) were heated in N,N-dimethylformamide (2 ml) at 120° C. for 7 minutes. The reaction mixture was allowed to cool to ambient temperature and then extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 4:1) to give Compound No. A1 of Table A (210 mg, 40% yield) as a solid foam.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (eluent: hexane/ethyl acetate 4:1)
  5. customto give Compound No

Sources & evidence

ORD record
ord-37ec0dd68a264f2caf7ebd0c6123e459
Source dataset
uspto-grants-2014_09
Patent number
US08822502B2

Reaction notes

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