Sodium Trifluoroacetate → HCID 14774831, compound

HRID 846517Notes

Reaction equation

HRID 846517 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-])=O.[Na+].[Cl:9][C:10]1[CH:15]=C(Cl)[C:13]([O:17][CH3:18])=[CH:12][C:11]=1[N:19]1[C:23](=[O:24])[N:22]([CH2:25][CH2:26][CH3:27])[N:21]=[N:20]1.BrC1C(OC)=CC(N2C(=O)N(CCC)N=N2)=C(Cl)C=1>CN(C)C(=O)C.[Cu]I>[Cl:9][C:10]1[CH:15]=[C:3]([C:2]([F:7])([F:6])[F:1])[C:13]([O:17][CH3:18])=[CH:12][C:11]=1[N:19]1[C:23](=[O:24])[N:22]([CH2:25][CH2:26][CH3:27])[N:21]=[N:20]1

Participants

6

Reactant 3

HCID 517019Sodium TrifluoroacetateHCID 3437914HCID 3437914, compoundHCID 14349356HCID 14349356, compound2×

Product 1

HCID 14774831HCID 14774831, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

Under a dry nitrogen atmosphere a stirred mixture of 6.0 g (0.044 mole) of sodium trifluoroacetate and 4.18 g (0.022 mole) of copper(I) iodide in 40 mL of N,N-dimethylacetamide was heated at 150° C. To the hot mixture was added 3.3 9 (0.011 mole) of 1-(4-bromo-2-chloro-5-methoxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one (compound 12). After complete addition, the hot mixture was stirred for 3 hours then allowed to cool to room temperature. The mixture was filtered and the filtrate diluted with ice water to form a precipitate. The solid was collected by filtration and purified, first by column chromatography on silica gel eluting with methylene chloride:heptane (80:20), then by recrystallization from heptane to yield 0.7 g of 1-(2-chloro-5-methoxy-4-trifluoromethylphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one, mp 82°-83° C.

Workup

  1. additionAfter complete addition
  2. temperatureto cool to room temperature
  3. filtrationThe mixture was filtered
  4. additionthe filtrate diluted with ice water
  5. customto form a precipitate
  6. filtrationThe solid was collected by filtration
  7. custompurified, first by column chromatography on silica gel eluting with methylene chloride:heptane (80:20)
  8. customby recrystallization from heptane

Sources & evidence

ORD record
ord-eec2a7c5af11463aa4183e1087e01d48
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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