Triethylamine → N-(7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)aminothiocarbonylperhydropyridazine

HRID 1762024Notes

Reaction equation

HRID 1762024 reaction equation
I.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.[F:15][C:16]1[C:29]([N:30]=[C:31]=[S:32])=[CH:28][C:19]2[N:20]([CH2:25][CH2:26][CH3:27])[C:21](=[O:24])[CH2:22][O:23][C:18]=2[CH:17]=1.CCCCCCC>C(Cl)Cl>[F:15][C:16]1[C:29]([NH:30][C:31]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]2)=[S:32])=[CH:28][C:19]2[N:20]([CH2:25][CH2:26][CH3:27])[C:21](=[O:24])[CH2:22][O:23][C:18]=2[CH:17]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 12314334Perhydropyridazine hydroiodideHCID 14461654(7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)isothio-cyanate

Product 1

HCID 14461655N-(7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)aminothiocarbonylperhydropyridazineYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-25 °C

Procedure

To a stirred, cold (-20° C.) solution of 11.3 g (0.0529 mole) of perhydropyridazine hydroiodide in 200 mL of methylene chloride was added 16.1 g (0.159 mole) of triethylamine. While maintaining a reaction temperature of -25° C., a solution of 12.8 g (0.0481 mole) of (7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)isothio-cyanate in methylene chloride was added. After complete addition, the reaction mixture was stirred at -20° C. for 2.5 hours. The solvent was removed from the mixture by evaporation under reduced pressure leaving a residue. This residue was partitioned between ethyl acetate and water. The organic phase was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving an oily solid residue. This oily solid was dissolved in methylene chloride to which was added n-heptane, causing a precipitate to form. The precipitate was collected by filtration and was dried to yield 12.0 g of N-(7-fluoro-4-propyl-2H- 1,4-benzoxazin-3(4H)-on-6yl)aminothiocar-bonylperhydropyridazine.

Workup

  1. additionAfter complete addition
  2. customThe solvent was removed from the mixture by evaporation under reduced pressure
  3. customleaving a residue
  4. customThis residue was partitioned between ethyl acetate and 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 an oily solid residue
  9. customto form
  10. filtrationThe precipitate was collected by filtration
  11. customwas dried

Sources & evidence

ORD record
ord-5294f4760c454f0fac09cda9ee1489a0
Source dataset
uspto-grants-1989_05
Patent number
US04830659

Reaction notes

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