N-bromobutanimide → HCID 57550202, compound

HRID 1716833Notes

Reaction equation

HRID 1716833 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:23]=[CH:22][C:11]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)[O:6][CH:7]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:24][C:7]1[O:6][C:5]([C:8]2[CH:23]=[CH:22][C:11]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[N:4][C:3]=1[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57550195HCID 57550195, compound

Product 1

HCID 57550202HCID 57550202, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-{4-[4-(chloromethyl)-1,3-oxazol-2-yl]benzyl}-1H-benzimidazole (0.40 g, 1.24 mmol) in dry chloroform was treated with N-bromosuccinimide (NBS) (0.24 g, 1.36 mmol), stirred at room temperature for 1 h and concentrated in vacuo. The resultant residue was partitioned between CH2Cl2 and water. The organic phase was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. This residue was purified by column chromatography (silica, CH2Cl2:MeOH 98:2) to afford the title compound in 56% yield, identified by NMR and mass spectral analyses. 1H NMR (300 MHz, DMSO-d6): 8.43 (s, 1H), 7.93 (m, 2H), 7.59-7.76 (m, 1H), 7.47-7.53 (m, 1H), 7.45 (m, 2H), 7.10-7.31 (m, 2H), 5.60 (s, 2H), 4.65 (s, 2H). LCMS (ESI+) 402, 404 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was partitioned between CH2Cl2 and water
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThis residue was purified by column chromatography (silica, CH2Cl2:MeOH 98:2)

Sources & evidence

ORD record
ord-f626f782d6654e88a816fc4196873e66
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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