N-bromobutanimide → HCID 23113861, compound

HRID 1787201Notes

Reaction equation

HRID 1787201 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[CH:15]=[C:16]([NH2:21])[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:22]N1C(=O)CCC1=O>C(#N)C>[Br:22][C:15]1[C:14]2[CH:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[CH2:11][O:12][C:13]=2[C:18]([CH3:19])=[C:17]([CH3:20])[C:16]=1[NH2:21]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68707501HCID 68707501, compound

Product 1

HCID 23113861HCID 23113861, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(4-isopropylphenyl)-6,7-dimethyl-2,3-dihydro-1-benzofuran-5-amine synthesized in Reference Example 31 (5.62 g, 21.1 mmol) in acetonitrile (60 mL), was added N-bromosuccinimide (3.76 g, 21.1 mmol) at −20° C., and the mixture was stirred at the same temperature for 10 minutes. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 0.90 g (yield 34%) of the title compound. Melting point: 191-193° C. (hexane-ethyl acetate).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-e25453950bd149adb42c91e7999b74e8
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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