Dimethylformamide → HCID 86618076, compound

HRID 1986596Notes

Reaction equation

HRID 1986596 reaction equation
Cl[C:2]1[C:7]2[N:8]=[CH:9][C:10]3[N:11]([CH2:12][N:13]([O:15][CH3:16])[CH:14]=3)[C:6]=2[N:5]([CH2:17][CH2:18][CH3:19])[CH2:4][C:3]=1[CH3:20].CN(C)C=O.[N-:26]=[N+:27]=[N-:28].[Na+]>C1(C)C=CC=CC=1>[N:26]([C:2]1[C:7]2[N:8]=[CH:9][C:10]3[N:11]([CH2:12][N:13]([O:15][CH3:16])[CH:14]=3)[C:6]=2[N:5]([CH2:17][CH2:18][CH3:19])[CH2:4][C:3]=1[CH3:20])=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 68867784HCID 68867784, compound

Product 1

HCID 86618076HCID 86618076, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

1.5 g of intermediate A1 are stirred into 10 ml N,N-dimethylformamide. 1 g NaN3 is added at room temperature. The mixture is heated up to 60° C. and stirred for 5 hours. 100 ml toluol are added. The organic layer is separated and washed with 3×30 ml water. 90 ml of the solvent are removed. The reaction product precipitates. The crude product is purified by crystallisation from toluol.

Workup

  1. customThe organic layer is separated
  2. washwashed with 3×30 ml water
  3. custom90 ml of the solvent are removed
  4. customThe reaction product precipitates
  5. customThe crude product is purified by crystallisation from toluol

Sources & evidence

ORD record
ord-f1d3918729744fd6adbe02b7c675d981
Source dataset
uspto-grants-2009_06
Patent number
US07550465B2

Reaction notes

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