Hydrochloric Acid → HCID 14099378, compound

HRID 569692Notes

Reaction equation

HRID 569692 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1.I[CH2:16][CH2:17][CH3:18].Cl>CN(C)C=O>[F:3][C:4]1[CH:14]=[CH:13][C:7]2[N:8]([CH2:16][CH2:17][CH3:18])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 336431-IodopropaneHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 14099378HCID 14099378, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

Under a dry argon atmosphere 2.7 grams of a 60% suspension of sodium hydride in oil (0.068 mole of sodium hydride) was waashed with petroleum ether to remove the oil. To the washed sodium hydride was added 50 ml of N,N-dimethylformamide (DMF), and the mixture was stirred. A solution of 7-fluoro-2H-1,4-benzoxazin-3 (4H)-one (10.0 grams, 0.060 mole) in 50 ml of DMF was added. This mixture was warmed to approximately 40° C. for 30 minutes, and then was cooled to room temperature. A solution of 11.2 grams (0.066 mole) of 1-iodopropane in 10 ml of DMF was added, and the mixture was stirred at room temperature for approximately 18 hours. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 10.0 grams of 7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one as an oil.

Workup

  1. customto remove the oil
  2. additionTo the washed sodium hydride was added 50 ml of N,N-dimethylformamide (DMF)
  3. temperaturewas cooled to room temperature
  4. stirringthe mixture was stirred at room temperature for approximately 18 hours
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3cec514fa8e14908ac3d59703c972691
Source dataset
uspto-grants-1988_03
Patent number
US04734124

Reaction notes

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