Water → HCID 15079203, compound

HRID 2092030Notes

Reaction equation

HRID 2092030 reaction equation
Cl[CH2:2][C:3]1[N:7]([CH3:8])[N:6]=[N:5][N:4]=1.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K].[I-].[Na+].O>CN(C)C=O>[CH3:8][N:7]1[C:3]([CH2:2][N:13]2[C:9](=[O:19])[C:10]3[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:14])=[N:4][N:5]=[N:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 122050865-(chloromethyl)-1-methyl-1H-1,2,3,4-tetrazoleHCID 24194345Phthalimide potassium salt

Product 1

HCID 15079203HCID 15079203, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Chloromethyl)-1-methyl-1H-tetrazole (a crude product 6.9 g prepared in accordance with Chemical & Pharmaceutical Bulletin, 37(2), 322-6:1989), was dissolved in 50 mL of dimethylformamide and stirred with potassium phthalimide (5.00 g, 27.0 mmol) and sodium iodide (391 mg, 2.60 mmol) at room temperature for 17 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the desired product (550 mg, 4% yield, two steps).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ab67eff9325a4cd4ba63a6a5fd4a98c5
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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