N-bromobutanimide → HCID 57963064, compound

HRID 509955Notes

Reaction equation

HRID 509955 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 (78, 151 g, 650 mmol) in 4 L of acetonitrile under 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 (79, 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-ec54f8972c3f41e8884e7261de519ef9
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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