Dimethyl Sulfoxide → HCID 18615635, compound

HRID 1265365Notes

Reaction equation

HRID 1265365 reaction equation
[Cl:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]([C:6]([N:10]2C(=O)C3=CC=CC=C3C2=O)=[C:7]([F:9])[CH:8]=1)[NH2:5].NN.[OH2:25].CS(C)=[O:28]>>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[C:6]([NH2:10])=[C:4]([N+:5]([O-:28])=[O:25])[C:3]=1[O:21][CH3:22]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 9321HydrazineHCID 18615634HCID 18615634, compound

Product 1

HCID 18615635HCID 18615635, compound

Procedure

3-Chloro-5-fluoro-2-methoxy-6-(phthalimido)aniline (0.6 g, 1.7 mmol) was dissolved in dimethylsulfoxide (3 ml) and anhydrous hydrazine (0.22 g, 6.8 mmol) was added. The solution was stirred at ambient temperature for 12 hr under a stream of nitrogen. Water was added and the product extracted with ether. The organic layer was washed with water, dried (anhydrous sodium sulfate), and evaporated to furnish the title compound (0.22 g). 1H NMR (CDCl3, 300 MHz) 3.98 (3H, s), 5.09 (2H, br s), 7.2 (1H, d, J=10.5 Hz) ppm.

Workup

  1. extractionthe product extracted with ether
  2. washThe organic layer was washed with water
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-7fd3a40a7bac4394a41f79498919e1cd
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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