Nitrofungin → HCID 20537903, compound

HRID 1155760Notes

Reaction equation

HRID 1155760 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][N:16]=1>C1COCC1.O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[Cl:1])=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 12074NitrofunginHCID 24758Sodium hydrideHCID 64246615-(Bromomethyl)-2-chloropyridine

Product 1

HCID 20537903HCID 20537903, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Chloro-4-nitrophenol (17.4 mmol) in 15 ml of THF is slowly added to a stirring suspension of sodium hydride (17.4 mmol) in 25 ml of THF. After gas evolution has ceased, 2-chloro-5-bromomethylpyridine is added and the mixture is heated under reflux overnight. The reaction is diluted with water, extracted with chloroform, washed with water, dried and stripped to give 2-chloro-5-(2-chloro-4-nitrophenoxy)methylpyridine.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. extractionextracted with chloroform
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9d88b87fcce641edb3c7de8afa9f3ca0
Source dataset
uspto-grants-1982_06
Patent number
US04332944

Reaction notes

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