Water → HCID 14551615, compound

HRID 1608034Notes

Reaction equation

HRID 1608034 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[NH:11][N:10]=[N:9]2)=[C:4]([F:14])[CH:3]=1.[F:15][CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([CH2:18][CH2:17][CH2:16][F:15])[N:10]=[N:9]2)=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 1356217974-chloro-2-fluorophenyl-1,4-dihydro-5H-tetrazol-5-one

Product 1

HCID 14551615HCID 14551615, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4.7 g (0.022 mole) of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazol-5-one, 4.0 g (0.028 mole) of 3-fluoropropyl bromide and 4.0 g (0.028 mole) of potassium carbonate in 60 ml of dimethylformamide was heated at 60° C. for 16 hours. The reaction mixture was poured into water and the mixture extracted with diethyl ether. The combined ether extract was 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 3.5 g of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one; m.p. 62°-63° C. The reaction was repeated several times.

Workup

  1. extractionthe mixture extracted with diethyl ether
  2. extractionThe combined ether extract
  3. dry with materialwas 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-5adbc0dbb0c24051b340b1554a48150e
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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