Dinitrofluorobenzene → HCID 13825162, compound

HRID 2352015Notes

Reaction equation

HRID 2352015 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([SH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[N+:16]([C:19]1[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[CH:22]=[CH:21][C:20]=1F)([O-:18])=[O:17]>C(O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([S:13][C:20]2[CH:21]=[CH:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][C:19]=2[N+:16]([O-:18])=[O:17])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 14798Sodium HydroxideHCID 138222652-t-butyl-5-mercapto-4-methyl-3(2H)-pyridazinone

Product 1

HCID 13825162HCID 13825162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2.0 g (0.01 mol) of the crude product of 2-tert.-butyl-5-mercapto-4-methyl-3(2H)-pyridazinone dissolved in 15 ml of ethanol was added 1.5 ml of 20% sodium hydroxide under stirring at room temperature. After stirring for additional 15 minutes at room temperature, the resulting mixture was added dropwise with a solution of 1.4 g of 2,4-dinitrofluorobenzene dissolved in 5 ml of ethanol and stirred for 10 minutes at room temperature. Crystalline precipitates were collected by filtration, washed with 50 ml of water and 50 ml of ethanol and then recrystallized from 50 ml of benzene to give 2.0 g of 2-tert.-butyl-4-methyl-5-(2',4'-dinitrophenylthio)-3(2H)-pyridazinone.

Workup

  1. stirringAfter stirring for additional 15 minutes at room temperature
  2. stirringstirred for 10 minutes at room temperature
  3. customCrystalline precipitates
  4. filtrationwere collected by filtration
  5. washwashed with 50 ml of water and 50 ml of ethanol
  6. customrecrystallized from 50 ml of benzene

Sources & evidence

ORD record
ord-edbb8510dc7b4c83ace41f9ad7bc7460
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

Loading…