N-bromobutanimide → HCID 57963064, compound

HRID 1775180Notes

Reaction equation

HRID 1775180 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:3]1[CH:4]=[CH:5][C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 17965116HCID 17965116, compound

Product 1

HCID 57963064HCID 57963064, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (6-fluoro-pyridin-2-yl)-(4-methoxy-benzyl)-amine (61, 151 g, 650 mmol) in 4 L of acetonitrile under an atmosphere of nitrogen, N-bromosuccinimide (116 g, 650 mmol) was added in portions. After reacting for 2 hours, the solvent was removed under vacuum and the residue taken up in ethyl acetate, then poured into aqueous sodium thiosulfate. The organic layer was washed with warm water, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was crystallized from heptane to provide the desired compound (62, 172 g, 553 mmol, 85% yield).

Workup

  1. customthe solvent was removed under vacuum
  2. additionpoured into aqueous sodium thiosulfate
  3. washThe organic layer was washed with warm water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum
  7. customThe resulting material was crystallized from heptane

Sources & evidence

ORD record
ord-8ddd7d5269e946a697fcc1254eb50ea1
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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