Potassium Carbonate → HCID 19912203, compound

HRID 1090997Notes

Reaction equation

HRID 1090997 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([S:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N:17]1[C:21](=[O:22])[N:20]([CH:23]([F:25])[F:24])[C:19]([CH3:26])=[N:18]1.C(=O)([O-])[O-].[K+].[K+].[CH3:33][CH:34](Br)[C:35]([O:37][CH3:38])=[O:36].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([N:17]2[C:21](=[O:22])[N:20]([CH:23]([F:24])[F:25])[C:19]([CH3:26])=[N:18]2)=[CH:4][C:5]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:34]([CH3:33])[C:35]([O:37][CH3:38])=[O:36])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 95576Methyl 2-bromopropionateHCID 19912207HCID 19912207, compound

Product 1

HCID 19912203HCID 19912203, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 1.5 g (0.0036 mole) of 1-[2,4-dichloro-5-(4-hydroxyphenylthio)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, 0.75 g (0.0054 mole) of potassium carbonate, 0.90 g (0.0054 mole) of methyl DL-2-bromopropionate, and 0.20 g (8×10-4 mole) of 18-crown-6 in 30 mL of N,N-dimethylformamide was heated at 100°-120° C. for approximately 18 hours. The reaction mixture was allowed to cool and was poured into ice-water. This aqueous mixture was extracted with diethyl ether and ethyl acetate. The organic extracts were combined and washed with water. The organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure, leaving a yellow oil. This oil was purified by column chromatography on silica gel, eluting with diethyl ether:petroleum ether (40:60) to yield 0.83 g of methyl 2-[4-[2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl- 5-oxo-1H-1,2,4-triazol-1-yl)phenylthio]phenoxy]propionate as a solid, m.p. 100°-101° C. The nmr spectrum was consistent with the proposed compound.

Workup

  1. temperaturewas heated at 100°-120° C. for approximately 18 hours
  2. temperatureto cool
  3. extractionThis aqueous mixture was extracted with diethyl ether and ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationwas filtered
  7. customThe filtrate was evaporated under reduced pressure
  8. customleaving a yellow oil
  9. customThis oil was purified by column chromatography on silica gel
  10. washeluting with diethyl ether:petroleum ether (40:60)

Sources & evidence

ORD record
ord-d6fba850e700472b8b9a430cea9b1ad2
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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