Water → HCID 178500188, compound

HRID 40429

Reaction equation

HRID 40429 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])#[N:2].[Cl-].C([NH+](CC)CC)C.[N-:19]=[N+:20]=[N-:21].[Na+].O>C1(C)C=CC=CC=1>[NH:2]1[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[N:21][N:20]=[N:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 554130Methyl 5-cyanopentanoateHCID 12698378Triethylazanium chloride

Product 1

HCID 178500188HCID 178500188, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 5-cyanopentanoate (4.8 g, 34 mmol) is dissolved in toluene, triethylammonium chloride (14 g, 102 mmol) and sodium azide (6.63, 102 mmol) is added. The mixture is heated to reflux for overnight. The reaction mixture is cooled to room temperature, water is added to extract (3×100 mL) methyl 5-tetrazol-5-ylpentanoate from the organic. To the aqueous phase, concentrate HCl is added to adjust pH to 2. The product is extracted from the aqueous solution with EtOAc (3×50 mL). The organic is combined, dried and concentrated to yield 4.25 g (68%) of methyl 5-tetrazol-5-ylpentanoate.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for overnight
  3. extractionto extract (3×100 mL) methyl 5-tetrazol-5-ylpentanoate from the organic
  4. concentrationTo the aqueous phase, concentrate HCl
  5. additionis added
  6. extractionThe product is extracted from the aqueous solution with EtOAc (3×50 mL)
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7cde7874cf74436290aebec88000a3ab
Source dataset
uspto-grants-2013_09
Patent number
US08529882B2

Linked notes

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