Water → HCID 46945966, compound

HRID 2370593Notes

Reaction equation

HRID 2370593 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[CH3:12][C:13]1([CH3:20])[NH:17][C:16](=[O:18])[NH:15][C:14]1=[O:19].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:12][C:13]1([CH3:20])[NH:17][C:16](=[O:18])[N:15]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[C:14]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6491DimethylhydantoinHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 46945966HCID 46945966, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2-nitrotoluene (1.55 g, 10 mmoles), 5,5-dimethylhydantoin (1.28 g, 10 mmoles), K2CO3 (1.38 g, 10 mmoles) in DMF (15 ml) is introduced into a vial intended to be placed in a microwave oven and irradiated at 100° C. for 70 minutes, under magnetic stirring. The reaction mixture is then poured into water (200 ml) and extracted with AcOEt (2×75 ml). The organic phases are combined, washed with salt water, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by chromatography on a silica column (eluent: Heptane/AcOEt:7/3). The expected compound is obtained in the form of a white solid with a yield of 25% (666 mg). Melting point: 177-178° C.

Workup

  1. additionis introduced into
  2. customto be placed in a microwave oven
  3. customirradiated at 100° C. for 70 minutes, under magnetic stirring
  4. extractionextracted with AcOEt (2×75 ml)
  5. washwashed with salt water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customthe residue is purified by chromatography on a silica column (eluent: Heptane/AcOEt:7/3)

Sources & evidence

ORD record
ord-70d82c744e5f48ca9d940dffe9b79d75
Source dataset
uspto-grants-2014_04
Patent number
US08710091B2

Reaction notes

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