N-bromobutanimide → HCID 18350648, compound

HRID 430475Notes

Reaction equation

HRID 430475 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:30])=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH2:11][NH:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[C:18](=[O:19])[O:17][CH2:16]3)[CH:7]=1.[Br:31]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Br:31][C:14]1[C:13]([NH:12][CH2:11][C:10]([OH:27])([C:23]([F:24])([F:26])[F:25])[CH2:9][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[OH:30])([CH3:28])[CH3:29])=[CH:22][CH:21]=[C:20]2[C:15]=1[CH2:16][O:17][C:18]2=[O:19]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 9888750HCID 9888750, compound

Product 1

HCID 18350648HCID 18350648, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

55 mg of (−)-5-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylamino]-phthalide is mixed under nitrogen in 1 ml of dimethylformamide at 2° C. with 18 mg of N-bromosuccinimide. After 2 hours at this temperature, it is diluted with 20 ml of ethyl acetate, extracted with water, and the organic phase is dried (Na2SO4) and concentrated by evaporation. With chromatography on silica gel, the title compound in crystalline form is eluted with hexane/ethyl acetate (4:1), flash point 228-232° C.

Workup

  1. extractionextracted with water
  2. dry with materialthe organic phase is dried (Na2SO4)
  3. concentrationconcentrated by evaporation
  4. washWith chromatography on silica gel, the title compound in crystalline form is eluted with hexane/ethyl acetate (4:1), flash point 228-232° C.

Sources & evidence

ORD record
ord-2d55ffac72724c0184c9dee35a1d70c3
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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