Sodium Iodide → HCID 178497366, compound

HRID 1796341Notes

Reaction equation

HRID 1796341 reaction equation
Cl[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:5]=2[N:4]=1.[Na+].[I-].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(#[N:26])C>>[O:21]1[CH2:22][CH2:23][N:18]([NH:26][CH2:2][C:3]2[NH:7][C:6]3[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:5]=3[N:4]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 8083MorpholineHCID 178497357HCID 178497357, compound

Product 1

HCID 178497366HCID 178497366, compoundYield 81%

Procedure

Methyl 2-(chloromethyl)-1H-benzimidazole-5-carboxylate (5) (0.5 g, 2.2 mmole), NaI (30 mg, 0.2 mmole), in 25 ml of anhydrous acetonitrile, add morpholine (0.48 ml, 5.50 mmole) and stir at ambient temperature for 5 hours. The solution was concentrated under reduced pressure and the resulting yellow solid redissolved in dichloromethane (20 ml) and washed with 10 ml of saturated bicarbonate solution. The organics were dried over anhydrous sodium sulfate and then concentrated to yield a fluffy solid (0.5 g, yield 81%) of 6.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe resulting yellow solid redissolved in dichloromethane (20 ml)
  3. washwashed with 10 ml of saturated bicarbonate solution
  4. dry with materialThe organics were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64118a24b934426bb563dbfe1b57c113
Source dataset
uspto-grants-2006_04
Patent number
US07030150B2

Reaction notes

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