Nitric Acid → 4-chloro-2-fluoro-5-nitrophenyl-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

HRID 1608035Notes

Reaction equation

HRID 1608035 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][CH2:15][CH2:16][F:17])[N:10]=[N:9]2)=[C:4]([F:18])[CH:3]=1.[N+:19]([O-])([OH:21])=[O:20]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][CH2:15][CH2:16][F:17])[N:10]=[N:9]2)=[C:4]([F:18])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 14551615HCID 14551615, compound

Product 1

HCID 145516164-chloro-2-fluoro-5-nitrophenyl-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 3.1 g (0.011 mole) of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one in 5 ml of concentrated sulfuric acid was added dropwise 0.9 ml (0.011 mole) of 70% nitric acid. Upon completion of addition the reaction mixture was stirred for two hours at ambient temperature then was poured into ice-water. The mixture was extracted with diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was dissolved in methylene chloride and passed through a pad of silica gel. The eluate was concentrated under reduced pressure to yield 2.8 g of 1-(4-chloro-2-fluoro-5-nitrophenyl-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one; m.p. 80°-81° C. The reaction was repeated several times.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionThe mixture was extracted with diethyl ether
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue
  6. dissolutionThe residue was dissolved in methylene chloride
  7. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ea51c38dfdcd43b8bfdef0a72550d18e
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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