N-bromobutanimide → HCID 20080769, compound

HRID 1653844Notes

Reaction equation

HRID 1653844 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:24]=[CH:23][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:19](=[O:20])[CH:18]=[C:17]([CH3:21])[NH:16][C:15]=3[CH3:22])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:27][C:18]1[C:19](=[O:20])[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:25])[F:26])=[CH:24][CH:23]=3)=[CH:9][CH:10]=2)=[C:15]([CH3:22])[NH:16][C:17]=1[CH3:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20080798HCID 20080798, compound

Product 1

HCID 20080769HCID 20080769, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred suspension of 3-(4-(4-trifluoromethylphenoxy)phenyl)-2,6-dimethyl pyridin-4(1H)-one (4.12 g) in chloroform (50 ml) at room temperature was added N-bromosuccinimide (2.25 g). After 2 hr the mixture was filtered and the solid washed with chlorofrom and dried in vacuo. Recrystallisation from DMF afforded the title compound (2.18 g), m.p. 304°-305°, NMR δH (d6 -DMSO) 7.70 (2H, dd, J 5, 0.5 Hz), 7.0-7.3 (6H, m), 2.42 (3H, s), 2.1 (3H, s).

Workup

  1. filtrationAfter 2 hr the mixture was filtered
  2. washthe solid washed with chlorofrom
  3. customdried in vacuo
  4. customRecrystallisation from DMF

Sources & evidence

ORD record
ord-d9ae4a119f5241f5baa48c18955c058a
Source dataset
uspto-grants-1995_04
Patent number
US05403934

Reaction notes

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