Isobutyl iodide → 7-fluoro4-isobutyl-2H-1,4-benzoxazin-3(4H)-one

HRID 2255184Notes

Reaction equation

HRID 2255184 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.[CH2:15](I)[CH:16]([CH3:18])[CH3:17]>CN(C)C=O>[F:3][C:4]1[CH:14]=[CH:13][C:7]2[N:8]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 137312957-fluoro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 190471647-fluoro4-isobutyl-2H-1,4-benzoxazin-3(4H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3.96 g (99 mmol) of hexanes washed 60% sodium hydride in 150 ml of N,N-dimethylformamide was added portionwise as a solid 15 g (90 mmol) of 7-fluoro-2H-1,4-benzoxazin-3(4H)-one. When the addition was complete the reaction was stirred at room temperature for 10 min, after which time 19.8 g (108 mmol) of isobutyl iodide was added. The reaction was then stirred overnight before quenching onto 200 ml of water. The aqueous phase was extracted with EtOAc (2×150 ml) and the combined organics were dried over Na2SO4, filtered and evaporated in vacuo to give the desired alkylated product, as a yellow oil (13 g, 65% yield).

Workup

  1. additionWhen the addition
  2. stirringThe reaction was then stirred overnight
  3. custombefore quenching onto 200 ml of water
  4. extractionThe aqueous phase was extracted with EtOAc (2×150 ml)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give the desired alkylated product

Sources & evidence

ORD record
ord-96fa3999b9b647e2923fb0aa70ddfb65
Source dataset
uspto-grants-1993_08
Patent number
US05238908

Reaction notes

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