Ammonia → 5-iodo-2-pyrrolidin-1-yl-1H-benzimidazole

HRID 2112825Notes

Reaction equation

HRID 2112825 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7]([N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[Na+].[I-:17].NCCN.N>O.[Cu]I.O1CCOCC1>[I:17][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7]([N:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 3301EthylenediamineHCID 5238Sodium IodideHCID 178419330HCID 178419330, compound

Product 1

HCID 1785065395-iodo-2-pyrrolidin-1-yl-1H-benzimidazole

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

0.48 g (1.8 mmol) of 5-bromo-2-pyrrolidin-1-yl-1H-benzimidazole and 34 mg (0.18 mmol) of CuI are placed in a round flask. The reaction vessel is flushed with argon. Then 0.54 g (3.6 mmol) of NaI, 32 mg (0.36 mmol) of dimethylenediamine, and 3 mL of 1,4-dioxane are added under argon. The reaction mixture is stirred for 14 hours at 110° C. Subsequently, the cooled reaction mixture is combined with concentrated ammonia solution, diluted with water, and the precipitate formed is filtered off. The solid is stirred with methanol and again filtered. Yield: 0.3 g (53% of theoretical); C11H12IN3 (M=313.13); calc.: molpeak (M+H)+: 314; found: molpeak (M)+: 314.

Workup

  1. customThe reaction vessel is flushed with argon
  2. customSubsequently, the cooled reaction mixture
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. stirringThe solid is stirred with methanol
  6. filtrationagain filtered

Sources & evidence

ORD record
ord-03671c1e21084e4ab6761c9ecacc257f
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

Loading…