Pyridine → 9-(4-Chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione

HRID 1164710Notes

Reaction equation

HRID 1164710 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([NH:17][C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]2)=[S:19])=[C:10]([F:26])[CH:9]=1.[C:27](Cl)(Cl)=[S:28]>C(Cl)Cl>[Cl:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([N:17]=[C:18]2[N:20]3[N:21]([CH2:22][CH2:23][CH2:24][CH2:25]3)[C:27](=[S:28])[S:19]2)=[C:10]([F:26])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10040ThiophosgeneHCID 14622955N-(4-chloro-2-fluoro-5-nitrophenylaminothiocarbonyl)perhydropyridazine

Product 1

HCID 146229569-(4-Chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thioneYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

While maintaining a reaction temperature of -5° C., 7.75 g (0.0850 mole) of pyridine was added dropwise to a stirred solution of 9.0 g (0.028 mole) of N-(4-chloro-2-fluoro-5-nitrophenylaminothiocarbonyl)perhydropyridazine in 250 mL of methylene chloride. To this mixture was added dropwise 3.25 g (0.0282 mole) of thiophosgene. This mixture was stirred at -5° C. for 30 minutes, then was allowed to warm to room temperature and was stirred for approximately 18 hours. The reaction mixture was washed with an aqueous, 5% hydrochloric acid solution followed by an aqueous, saturated sodium chloride solution. The washed reaction mixture was dried over anhydrous magnesium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving a solid residue. The residue was purified by recrystallization to yield 4.5 g of 9-(4-chloro-2-fluoro-5-nitrophenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-thione, mp 171°-173° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for approximately 18 hours
  3. washThe reaction mixture was washed with an aqueous, 5% hydrochloric acid solution
  4. customThe washed reaction mixture
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. filtrationwas filtered
  7. customThe filtrate was evaporated under reduced pressure
  8. customleaving a solid residue
  9. customThe residue was purified by recrystallization

Sources & evidence

ORD record
ord-72d6f713c76e42a0a26e789d3967688f
Source dataset
uspto-grants-1990_03
Patent number
US04906281

Reaction notes

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