Propargyl bromide → 2,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 1506577Notes

Reaction equation

HRID 1506577 reaction equation
[F:1][C:2]1([F:17])[O:7][C:6]2[CH:8]=[C:9]([F:15])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[NH:4][C:3]1=[O:16].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]#[CH:27]>CN(C)C=O.[NH4+].[Cl-]>[F:17][C:2]1([F:1])[O:7][C:6]2[CH:8]=[C:9]([F:15])[C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:5]=2[N:4]([CH2:27][C:26]#[CH:25])[C:3]1=[O:16]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 668358542,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 871738852,2,7-trifluoro-6-nitro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 88.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To 2,2,7-trifluoro-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (6.9 g, 27.8 mmol) and potassium carbonate (4.61 g, 33.4 mmol) in dry N,N-Dimethylformamide at RT was dropwise added 3-bromoprop-1-yne (80 wt % in toluene; 4.96 g, 33.4 mmol). The resulting mixture was stirred at RT overnight. The reaction mixture was poured in saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined extracts were washed with aqueous NaCl solution, dried with Na2SO4, concentrated and chased with toluene to yield 7.06 g of the title compound as dark brown solid.

Workup

  1. customat RT
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with aqueous NaCl solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-566b188707bb4f7b97f52d6975f9b21c
Source dataset
uspto-grants-2015_12
Patent number
US09220268B2

Reaction notes

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