Sodium Azide → HCID 59843142, compound

HRID 2196523Notes

Reaction equation

HRID 2196523 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([N:13]2[C:17]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][C:15]([C:23]([F:26])([F:25])[F:24])=[N:14]2)[CH:8]=1)(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C=O)C>[N:27]([CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([N:13]2[C:17]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][C:15]([C:23]([F:26])([F:25])[F:24])=[N:14]2)[CH:8]=1)=[N+:28]=[N-:29]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59843169HCID 59843169, compound

Product 1

HCID 59843142HCID 59843142, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 38 (0.695 mmol) in DMF (4.6 mL) at room temperature was added sodium azide (136 mg, 2.085 mmol) drop wise. The resulting solution was allowed to stir for 1 h at 60° C. The mixture was quenched with water and extracted with ethyl acetate, washed with brine (two times), dried (MgSO4) filtered and concentrated. Compound 39 (205 mg, 88%) was isolated as a brown oil and used as is for the next step. LRMS (ESI): calc. 334.1; found 335.1 (MH)+.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washwashed with brine (two times)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7cf0f8644b824e28812baa1d3caa55ac
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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