p-Fluoronitrobenzene → HCID 15079649, compound

HRID 476509Notes

Reaction equation

HRID 476509 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[N:11]=[N:10]2)=[C:4]([F:19])[CH:3]=1.[H-].[Na+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[CH:6][C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH2:16][CH2:17][F:18])[N:11]=[N:10]2)=[C:4]([F:19])[CH:3]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 14774834HCID 14774834, compound

Product 1

HCID 15079649HCID 15079649, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 9.3 g (0.032 mole) of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one in approximately 30 ml of N,N-dimethylformamide was added to a stirred mixture of 1.5 g (0.030 mole) of sodium hydride (50% suspension in oil) in 100 ml of N,N-dimethylformamide. The mixture was stirred for 15 minutes and 4.50 g (0.0304 mole) of 4-fluoronitrobenzene was added. This mixture was stirred at room temperature for approximately 18 hours then was heated at 80° C. for five hours. The mixture was cooled, poured into ice water and was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a solid residue. This residue was purified by recrystallization from n-heptane to yield 8.1 g of 1-[4-chloro-2-fluoro-5-(4-nitrophenoxy)phenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one, m.p. 109°-110° C.

Workup

  1. stirringThis mixture was stirred at room temperature for approximately 18 hours
  2. temperatureThe mixture was cooled
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customto leave a solid residue
  8. customThis residue was purified by recrystallization from n-heptane

Sources & evidence

ORD record
ord-55150c9017714877b7f12085716d8368
Source dataset
uspto-grants-1989_12
Patent number
US04885025

Reaction notes

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