N-bromobutanimide → ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate

HRID 216601Notes

Reaction equation

HRID 216601 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N:21]2[CH:25]=[CH:24][N:23]=[C:22]2[S:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:13][CH:12]=1)#[N:10]>ClCCl>[Br:1][C:25]1[N:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([C:9]#[N:10])=[CH:12][CH:13]=2)[C:22]([S:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:23][CH:24]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59225848ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate

Product 1

HCID 59225908ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetateYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-bromosuccinimide (5.48 g, 30.82 mmol) was added in three portions to a solution of ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate (10.40 g, 30.82 mmol) in dichloromethane (150 mL) at 0° C. and then stirred at room temperature for 18 h. The mixture was washed with water (2×50 mL), saturated aqueous sodium chloride solution (50 mL), dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-50% EtOAc/hexanes) provided ethyl 2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate as an off-white solid (9.18 g, 71.5%).

Workup

  1. washThe mixture was washed with water (2×50 mL), saturated aqueous sodium chloride solution (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-363f9ef648de441db67fd702805b7b41
Source dataset
uspto-grants-2012_06
Patent number
US08193234B2

Reaction notes

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