Dimethylformamide → HCID 21904647, compound

HRID 643246Notes

Reaction equation

HRID 643246 reaction equation
CS(O[CH2:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([C:14]#[N:15])=[CH:9][C:8]=1[F:16])(=O)=O.[N-:17]=[N+:18]=[N-].[Na+].C[N:22](C=O)C>O>[N:15]([CH2:14][C:10]1[CH:11]=[C:12]([F:13])[C:7]([C:6]#[N:22])=[C:8]([F:16])[CH:9]=1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 21904603HCID 21904603, compound

Product 1

HCID 21904647HCID 21904647, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 4-cyano-2,6-difluorobenzyl methanesulfonate (1.61 g, 6.51 mmol; see step (iv) above) and sodium azide (0.72 g, 0.0111 mol) in 10 mL of water and 20 mL of DMF was stirred at room temperature overnight. The resultant was subsequently poured into 200 mL of water and extracted three times with diethyl ether. The combined ethereal phase was washed five times with water, dried (Na2SO4) and evaporated. A small sample was evaporated for NMR purposes and the product crystallised. The rest was evaporated cautiously but not until complete dryness. Yield (theoretically 1.26 g) was assumed to be almost quantitative based on NMR and analytical HPLC.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined ethereal phase was washed five times with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customA small sample was evaporated for NMR purposes
  6. customthe product crystallised
  7. customThe rest was evaporated cautiously but not until complete dryness
  8. customYield (theoretically 1.26 g)

Sources & evidence

ORD record
ord-d8e6219d76e947d7ba51da3acead54f2
Source dataset
uspto-grants-2010_04
Patent number
US07700582B2

Reaction notes

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