Potassium Carbonate → ethyl 3-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazol-1-yl]phenyl]propenoate

HRID 2072579Notes

Reaction equation

HRID 2072579 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:13](=[O:14])[NH:12][N:11]=[N:10]2)=[CH:4][C:3]=1[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[F:22][CH2:23][CH2:24][CH2:25]CS([O-])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:13](=[O:14])[N:12]([CH2:25][CH2:24][CH2:23][F:22])[N:11]=[N:10]2)=[CH:4][C:3]=1[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30293133-Fluoropropylmethane sulfonateHCID 136207185ethyl 3-[2-chloro-4-fluoro-5-(1,4-dihydro-5-oxo-5H-tetrazol-1-yl)phenyl]propenoate

Product 1

HCID 53785460ethyl 3-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazol-1-yl]phenyl]propenoateYield 24.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2.62 g (0.00830 mole) of ethyl 3-[2-chloro-4-fluoro-5-(1,4-dihydro-5-oxo-5H-tetrazol-1-yl)phenyl]propenoate in 20 mL of N,N-dimethylformamide was added 1.46 g (0.00939 mole) of 3-fluoropropylmethane sulfonate and 1.30 g (0.00939 mole) of potassium carbonate. The reaction mixture was heated at 50°-60° C. and was stirred at that temperature for approximately 18 hours. The mixture was cooled and was poured into ice water. This mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure to yield 0.76 g of ethyl 3-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-1,4-dihydro-5-oxo-5H-tetrazol -1yl]phenyl]propenoate as an oil, compound 4 of Table 1.

Workup

  1. temperatureThe reaction mixture was heated at 50°-60° C.
  2. temperatureThe mixture was cooled
  3. extractionThis mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. filtrationwas filtered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-50250b2f574b41e4ac89b7a00c6aec5c
Source dataset
uspto-grants-1990_04
Patent number
US04913724

Reaction notes

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