Dimethylformamide → HCID 4109869, compound

HRID 1701932Notes

Reaction equation

HRID 1701932 reaction equation
CN(C)C=[O:4].[F-].[K+].Cl[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1Cl)=[O:19]>C1(C)C=CC=CC=1>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]2[O:4][C:21]3[C:20](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18](=[O:19])[C:10]=2[CH:11]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 13120762HCID 13120762, compound

Product 1

HCID 4109869HCID 4109869, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 900 mL of dimethyl formamide, 165 mL of toluene, 65.6 g (1.13 mol) of anhydrous potassium fluoride, and 74.6 g (0.252 mol) of (2-chloro-5-nitrophenyl)(2-chlorophenyl)methanone was stirred and heated to reflux. It was dried by distilling out 170 mL of distillate, and then heated under reflux overnight. It was cooled in an ice bath and diluted with 1 l of water and 100 mL of hexane. After 1 hr the gold-colored precipitate was collected and dissolved in 300 mL of methylene chloride. The solution, after separation of water, was dried over sodium sulfate and concentrated in vacuo. The residue was slurried in ether (cold) to leave crude 2-nitroxanthene-9-one. The ether solution was concentrated in vacuo and the residue recrystallized from methanol to give the product, 60°-64°.

Workup

  1. temperatureheated to reflux
  2. customIt was dried
  3. distillationby distilling out 170 mL of distillate
  4. temperatureheated
  5. temperatureunder reflux overnight
  6. temperatureIt was cooled in an ice bath
  7. additiondiluted with 1 l of water and 100 mL of hexane
  8. customAfter 1 hr the gold-colored precipitate was collected
  9. dissolutiondissolved in 300 mL of methylene chloride
  10. customThe solution, after separation of water
  11. dry with materialwas dried over sodium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb286c76c67c464c8b40a12fcfec2985
Source dataset
uspto-grants-1983_04
Patent number
US04379765

Reaction notes

Loading…