Dimethylformamide → HCID 9795316, compound

HRID 585776Notes

Reaction equation

HRID 585776 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[O:11]1[CH2:16][CH2:15][N:14]([CH:17](O)[CH2:18]C)[CH2:13][CH2:12]1.[C:21](=O)([O-])[O-:22].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C.O>[O:11]1[CH2:12][CH2:13][N:14]([CH:17]([CH3:18])[CH2:21][O:22][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 567691HCID 567691, compound

Product 1

HCID 9795316HCID 9795316, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.57 g 2-fluoronitrobenzene, 0.65 g morpholino-propanol, 3.0 g caesium carbonate and 30 ml dimethylformamide are stirred for 2 days at room temperature in a closed 50 ml round-bottomed flask. One pours the suspension on to 50 ml water, extracts the aqueous phase 3 times with, in each case, 50 ml ethyl acetate and evaporates the combined organic phases on a rotoevaporator. For the removal of the dimethylformamide, which would disturb the chromatographic separation, the DMF-containing residue is again evaporated 2 to 3 times, together with some toluene, at 50° C. and 30 mbar vacuum. The oily residue is then purified on silica gel (0.04 to 0.063 mm) at 0.1 bar by flash chromatography. Once obtains 0.9 g of oil (82.4%).

Workup

  1. customevaporates the combined organic phases on a rotoevaporator
  2. customFor the removal of the dimethylformamide, which
  3. customthe chromatographic separation
  4. additionthe DMF-containing residue
  5. customis again evaporated 2 to 3 times
  6. customat 50° C.
  7. customThe oily residue is then purified on silica gel (0.04 to 0.063 mm) at 0.1 bar by flash chromatography

Sources & evidence

ORD record
ord-28b863cb45114a5387288a18a5a355bb
Source dataset
uspto-grants-2005_08
Patent number
US06933390B2

Reaction notes

Loading…