Dimethylformamide → HCID 59516971, compound

HRID 1161592Notes

Reaction equation

HRID 1161592 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[C:17]2[O:16][CH2:15][C:14](=[O:18])[NH:13][C:12]=2[CH:11]=[C:10]([CH:19]=[O:20])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+].[F:27][CH2:28][CH2:29]I>O>[F:27][CH2:28][CH2:29][N:13]1[C:12]2[CH:11]=[C:10]([CH:19]=[O:20])[CH:9]=[C:8]([O:7][CH3:6])[C:17]=2[O:16][CH2:15][C:14]1=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 18452465HCID 18452465, compound

Product 1

HCID 59516971HCID 59516971, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3 ml of a DMF solution containing 233 mg of 8-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboaldehyde [CAS No. 711021-34-0], 312 mg of potassium carbonate and 236 mg of 1-fluoro-2-iodoethane were added. The resulting mixture was stirred at room temperature for one day, and water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and then dried over anhydrous sodium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give 4-(2-fluoroethyl)-8-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboaldehyde (151 mg) as a white solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe desiccating agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-7e4f95d2dbcc442a8498307e8a229a41
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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