Ethyl Bromide → (1-(4-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)ethyl sulfide

HRID 1608039Notes

Reaction equation

HRID 1608039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[S:13])[NH:11][N:10]=[N:9]2)=[C:4]([F:14])[CH:3]=1.Br[CH2:16][CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)C>[CH2:16]([S:13][C:12]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[F:14])[N:9]=[N:10][N:11]=1)[CH3:17]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 178505829HCID 178505829, compound

Product 1

HCID 14551620(1-(4-chloro-2-fluorophenyl)-1H-tetrazol-5-yl)ethyl sulfideYield 81.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.75 g (0.0076 mole) of 1-(4-chloro-2-fluorophenyl)-1,4-dihydro-5H-tetrazol-5-thione, 0.57 ml (0.0076 mole) of bromoethane, and 1.6 g (0.012 mole) of potassium carbonate in 8 ml of acetone was stirred at room temperature for seven hours. The solvent was evaporated from the reaction mixture under reduced pressure leaving a residue. This residue was dissolved in diethyl ether and the organic solution was washed with water. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.6 g of (1-(4-chloro-2-fluorophenyl)-1H-tetrazol-5-yl) ethyl sulfide as a solid, m.p. 76°-79° C.

Workup

  1. customThe solvent was evaporated from the reaction mixture under reduced pressure
  2. customleaving a residue
  3. washthe organic solution was washed with water
  4. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a280ca4d37d7426f87e652ddc7c69646
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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