Water → 7-Fluoro-6-nitro-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one

HRID 1030961Notes

Reaction equation

HRID 1030961 reaction equation
[H-].[Na+].[F:3][C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1.[CH2:18](Br)[C:19]#[CH:20].O>CN(C)C=O>[F:3][C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:7]2[N:8]([CH2:20][C:19]#[CH:18])[C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 137312977-Fluoro-6-nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 137312997-Fluoro-6-nitro-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (0.06 g) in N,N-dimethylformamide (3 ml) is cooled to 0° C. 7-fluoro-3,4-dihydro-3-oxo-6-nitro-2H-1,4-benzoxazine (0.57 g) is added thereto at between 0° to 5° C., and the resultant mixture is stirred for 30 minutes. Propargyl bromide (0.35 g) is added to the mixture, which is gradually heated to room temperature, and the reaction is continued for 6 hours. After addition of water, the resultant mixture is extracted with ethyl acetate, and the extract is washed with water, dried and concentrated. The residue is purified by silica gel thin layer chromatography using a 1:1 mixture of ethyl acetate and n-hexane as the eluent to give 7-fluoro-3,4-dihydro-3-oxo-6-nitro-4-(2-propynyl)-2H-1,4-benzoxazine.

Workup

  1. temperatureis gradually heated to room temperature
  2. extractionthe resultant mixture is extracted with ethyl acetate
  3. washthe extract is washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel thin layer chromatography
  7. additiona 1:1 mixture of ethyl acetate and n-hexane as the eluent

Sources & evidence

ORD record
ord-395687079efc4708848f689c8a5d866f
Source dataset
uspto-grants-1992_04
Patent number
US05108488

Reaction notes

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