Ethyl bromoacetate → ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate

HRID 216600Notes

Reaction equation

HRID 216600 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[SH:15][C:16]1[N:17]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]#[N:32])=[CH:23][CH:22]=2)[CH:18]=[CH:19][N:20]=1>ClCCl>[C:31]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([N:17]2[CH:18]=[CH:19][N:20]=[C:16]2[S:15][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:22][CH:23]=1)#[N:32]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 178510004HCID 178510004, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (4.92 mL, 35.32 mmol), followed by ethyl bromoacetate (3.74 mL, 33.72 mmol) were added to a stirring slurry of 4-(2-mercapto-1H-imidazol-1-yl)-1-naphthonitrile (8.07 g, 32.11 mmol) in dichloromethane (60 mL) and stirring continued for 3 h. The mixture was washed with aqueous HCl solution (0.2M 100 mL), 50% saturated sodium chloride solution (50 mL), dried over sodium sulfate, filtered, and concentrated. Hexanes (100 mL) were added and the mixture concentrated to provide ethyl 2-(1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetate as a light-tan solid (10.47 g, (97%).

Workup

  1. washThe mixture was washed with aqueous HCl solution (0.2M 100 mL), 50% saturated sodium chloride solution (50 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionHexanes (100 mL) were added
  6. concentrationthe mixture concentrated

Sources & evidence

ORD record
ord-73463ae456e84f688b174c86caea972a
Source dataset
uspto-grants-2012_06
Patent number
US08193234B2

Reaction notes

Loading…