Water → (5-Bromo-6-chloro-pyridin-2-yl)-(4-chloro-benzyl)-amine

HRID 1952106Notes

Reaction equation

HRID 1952106 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[N:9]=2)=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.O>C(#N)C>[Br:17][C:11]1[CH:12]=[CH:13][C:8]([NH:7][CH2:6][C:5]2[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9][C:10]=1[Cl:14]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 57619237(4-Chloro-benzyl)-(6-chloro-pyridin-2-yl)-amine

Product 1

HCID 57619309(5-Bromo-6-chloro-pyridin-2-yl)-(4-chloro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To (4-chloro-benzyl)-(6-chloro-pyridin-2-yl)-amine (538, 4.00 g, 0.0158 mol) in acetonitrile (66.7 mL, 1.28 mol) under an atmosphere of nitrogen, N-bromosuccinimide (2.81 g, 0.0158 mol) in acetonitrile (20 mL) was added slowly. The reaction was stirred at room temperature overnight, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and crystallized with ethyl acetate in hexane to give a white solid (539, 2.60 g, 95.3%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customcrystallized with ethyl acetate in hexane
  5. customto give a white solid (539, 2.60 g, 95.3%)

Sources & evidence

ORD record
ord-7d0ce1a4ae404409816e3931d9084a9a
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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