Sodium Azide → HCID 68194709, compound

HRID 2370621Notes

Reaction equation

HRID 2370621 reaction equation
Cl[C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])[C:4](=[O:14])[C:5]2[C:6]([N:13]=1)=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=2.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C)C=O.O.[Cl-].[Na+].O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[N:3]1[C:4](=[O:14])[C:5]2[C:6](=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=2)[N:13]2[N:22]=[N:23][N:24]=[C:2]12

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 68194425HCID 68194425, compound

Product 1

HCID 68194709HCID 68194709, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 1B (0.175 g, 0.516 mmol) and sodium azide (0.037 g, 0.568 mmol) in N,N-dimethylformamide (5 mL) was heated at 70° C. for 1 hour. The reaction mixture was diluted with water and brine and extracted with ethyl acetate (2×). The combined organic layers were washed with brine (2×), dried over MgSO4, filtered, concentrated, and purified on a 12 g column using the ISCO Companion flash system eluting with CH2Cl2/ethyl acetate (95:5 to 90:10) to provide the title compound.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic layers were washed with brine (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on a 12 g column
  7. washeluting with CH2Cl2/ethyl acetate (95:5 to 90:10)

Sources & evidence

ORD record
ord-82ef74c9f2c64e59b77ba7e6e292a2ad
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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