Dimethylformamide → HCID 54775516, compound

HRID 1438342Notes

Reaction equation

HRID 1438342 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[F:11][CH2:12][CH2:13][N:14]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[N:15]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[F:11][CH2:12][CH2:13][N:14]1[C:18]([CH3:19])=[C:17]([CH:4]=[O:5])[C:16]([CH3:20])=[N:15]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 14449515HCID 14449515, compound

Product 1

HCID 54775516HCID 54775516, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To DMF (56 g, 0.75 mol) was added POCl3 (74.55 mL, 0.8 mol) at 0° C. After 30 minutes, to the formed Vilsmaier reagent was added 1-(2-fluoroethyl)-3,5-dimethyl-1H-pyrazole (88 g, 0.62 mol), and the reaction mixture was heated for 16 h at 80° C. The reaction mixture was diluted with dichloromethane (400 mL) and treated with potassium carbonate (600 g) in water (2 L) at 0° C. The organic layer was separated, passed through silica gel (10×10 cm), and evaporated. The liquid residue was crystallized from a mixture of hexane (100 mL) and ether (200 mL), separated by filtration, and dried in vacuo using an oil pump to give 26.3 g (24.9%) of the title product. Satisfactory C,H,N-analysis was obtained. 1H NMR (400 MHz, DMSO-d6): δ 2.33 (s, 3H), 2.48 (s, 3H), 4.36 (dt, J=28 Hz, J=5 Hz, 2H), 4.74 (dt, J=44 Hz, J=5 Hz, 2H), 9.85 (s, 1H). GC-MS calcd for C8H11FN2O: 170.09, found (M+): 170 m/z.

Workup

  1. customThe organic layer was separated
  2. customevaporated
  3. customThe liquid residue was crystallized from a mixture of hexane (100 mL) and ether (200 mL)
  4. customseparated by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dfaced859acb43eda7bae7b87ff84fc1
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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