Potassium Carbonate → 1-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one

HRID 257369Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20](=[O:21])[NH:19][N:18]=[N:17]3)=[C:12]([F:22])[CH:11]=2)=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][F:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20](=[O:21])[N:19]([CH2:24][CH2:25][CH2:26][F:27])[N:18]=[N:17]3)=[C:12]([F:22])[CH:11]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 7.0 g (0.023 mole) of 1-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-5H-tetrazol-5-one, 4.23 g (0.030 mole) of 1-bromo-3-fluoropropane, and 4.14 g (0.030 mole) of anhydrous potassium carbonate in 60 mL of N,N-dimethylformamide was heated at 70° C. for approximately seventeen hours. The mixture was allowed to cool to room temperature before being poured over ice. The solid that formed was removed by filtration and dried. This solid was then placed on a silica gel column and eluted with with methylene chloride. The product-containing fractions were combined and the solvents evaporated under reduced pressure, leaving 6.35 g of 1-[4-(4-fluorophenylmethoxy)-2-fluorophenyl]-1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-one, m.p. 86°-88° C.

Workup

temperatureto cool to room temperature
additionbefore being poured over ice
customThe solid that formed
customwas removed by filtration
customdried
washeluted with with methylene chloride
customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record: ord-2970a9c059fe40d9810bea62a5e3e9fb
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05262390

Reaction notes

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