Water → HCID 14551615, compound

HRID 846527Notes

Reaction equation

HRID 846527 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][NH:11][N:10]=[N:9]2)=[C:4]([F:13])[CH:3]=1.[F:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-:20].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:20])[N:11]([CH2:17][CH2:16][CH2:15][F:14])[N:10]=[N:9]2)=[C:4]([F:13])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 1785058281-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazole

Product 1

HCID 14551615HCID 14551615, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4.7 grams (0.22 mole) of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazole, 4.0 grams (0.028 mole) of 3-fluoropropyl bromide and 4.0 grams (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 grams 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-dde8f128ab5f4243b99e887e2d7e3387
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

Loading…