Ammonia → HCID 19882824, compound

HRID 846514Notes

Reaction equation

HRID 846514 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][CH3:18])[N:12]=[N:11]1.CC1C=CC(S(O)(=O)=O)=CC=1.[O:30]1[CH:34]=[CH:33][CH2:32][CH2:31]1.N>O1CCOCC1.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:31]2[CH2:32][CH2:33][CH2:34][O:30]2)=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][CH3:18])[N:12]=[N:11]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6101p-Toluenesulfonic acidHCID 709342,3-Dihydrofuran2×HCID 19882809HCID 19882809, compound

Product 1

HCID 19882824HCID 19882824, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 1.0 g (0.0035 mole) of 1-(2,4-dichloro-5-hydroxyphenyl)-1,4-dihydro-4-propyl-5H-tetrazol-5-one (Example 10, Step A) and 0.05 g (0.00026 mole) of 4-methylphenylsulfonic acid in 40 mL of p-dioxane was added slowly 0.88 g (0.0126 mole) of dihydrofuran in 20 mL of p-dioxane. The mixture was stirred at room temperature for approximately 18 hours, and an additional 0.88 g of dihydrofuran was added. The mixture was stirred at room temperature for an additional 48 hours. One mL of methanol saturated with ammonia was added to the mixture and stirring was continued for a short period of time. The reaction mixture was evaporated under reduced pressure to leave a residue. The residue was purified by column chromatography on silica gel, eluting with methylene chloride, to yield 0.58 g of 1-[2,4-dichloro-5-(2-tetrahydrofuranyloxy)phenyl]-1,4-dihydro-4-propyl-5H-tetrazol-5-one as a solid, mp 89°-90° C.

Workup

  1. stirringThe mixture was stirred at room temperature for an additional 48 hours
  2. stirringstirring
  3. waitwas continued for a short period of time
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customto leave a residue
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-b1ee827182fe4508bbbc4ecd2b9cf93e
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

Loading…