Sodium Azide → HCID 86662135, compound

HRID 1894719Notes

Reaction equation

HRID 1894719 reaction equation
Cl[CH2:2][C:3]1[S:4][C:5]([C:8]2[NH:12][N:11]=[CH:10][CH:9]=2)=[N:6][N:7]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C>[N:13]([CH2:2][C:3]1[S:4][C:5]([C:8]2[NH:12][N:11]=[CH:10][CH:9]=2)=[N:6][N:7]=1)=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 65694378HCID 65694378, compound

Product 1

HCID 86662135HCID 86662135, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 1 mL DMF solution of 2-(chloromethyl)-5-(1H-pyrazol-5-yl)-1,3,4-thiadiazole (58 mg, 0.29 mmol) was added sodium azide (20 mg, 0.30 mmol). Stirring continued at rt for 3 hr. The reaction mixture was concentrated and diluted with AcOEt and water. The organic layer was separated. The aqueous layer was extracted with AcOEt twice and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound (60 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with AcOEt and water
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with AcOEt twice
  5. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d97e3733f972474db729bc4983771838
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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