N-bromobutanimide → HCID 66823365, compound

HRID 2362184Notes

Reaction equation

HRID 2362184 reaction equation
[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[N:30]=[C:31]([C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:47])C(=O)C1>C(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:5][C:6](=[O:39])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][N:21]4[N:30]=[C:31]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[C:32]([Br:47])=[C:20]4[N:19]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 66719137HCID 66719137, compound

Product 1

HCID 66823365HCID 66823365, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 9-1 (104 mg, 0.2 mmol) in CHCl3 (5 mL) was added NBS (40 mg 0.22 mmol.) and the mixture was stirred at room temperature overnight. The mixture was diluted with 15 mL of DCM, the combined organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 83 mg of 9-3.

Workup

  1. washthe combined organic phase was washed with 0.1N HClaq and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep.TLC

Sources & evidence

ORD record
ord-faf59ee786e54c3c959cb2156aa990c1
Source dataset
uspto-grants-2014_04
Patent number
US08691825B2

Reaction notes

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