Triethylamine → N-(4-chloro-2-fluoro-5-nitrophenylaminothiocarbonyl)perhydropyridazine

HRID 1164709Notes

Reaction equation

I.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.[Cl:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([N:25]=[C:26]=[S:27])=[C:18]([F:28])[CH:17]=1>C(Cl)Cl>[Cl:15][C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([NH:25][C:26]([N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]2)=[S:27])=[C:18]([F:28])[CH:17]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a stirred, cold (-5° C.) solution of 8.56 g (0.0400 mole) of perhydropyridazine hydroiodide in 150 mL of methylene chloride was added dropwise 12.2 g (0.120 mole) of triethylamine. This mixture was stirred for approximately 30 minutes. A solution of 8.0 g (0.034 mole) of 4-chloro-2-fluoro-5-nitrophenylisothiocyanate in methylene chloride was added dropwise to the reaction mixture while maintaining a reaction temperature of -20° C. After complete addition, the reaction mixture was allowed to warm to room temperature and was stirred for two days. The solvent was removed from the mixture by evaporation under reduced pressure leaving a residue. The residue was subjected to column chromatography on silica gel, eluting with ethyl acetate:n-heptane (50:50), to yield 10.4 g of N-[(4-chloro-2-fluoro-5-nitrophenyl)aminothiocarbonyl]perhydropyridazine as a solid, mp 118°-120° C.

Workup

additionAfter complete addition
temperatureto warm to room temperature
stirringwas stirred for two days
customThe solvent was removed from the mixture by evaporation under reduced pressure
customleaving a residue
washeluting with ethyl acetate:n-heptane (50:50)

Sources & evidence

ORD record: ord-3063a2a00e5c4d53b3db28b9d051684c
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906281

Reaction notes

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