Triethylamine → 4-Chloro-2-fluoro-5-nitrophenylisothiocyanate

HRID 1164708Notes

Reaction equation

[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([NH2:6])=[C:4]([F:12])[CH:3]=1.[C:13](Cl)(Cl)=[S:14].C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C.CCCCCCC>[Cl:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:5]([N:6]=[C:13]=[S:14])=[C:4]([F:12])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.), stirring mixture of 12.0 g (0.0630 mole) of 4-chloro-2-fluoro-5-nitroaniline in 100 mL of methylene chloride was added dropwise 7.3 g (0.063 mole) of thiophosgene. While maintaining a temperature of 0° C., 13.2 g (0.130 mole) of triethylamine was added dropwise to the mixture. After complete addition, the mixture was allowed to warm to room temperature and stir for approximately 18 hours. The solvent was evaporated under reduced pressure leaving a residue. This residue was stirred in a mixture of ethyl acetate and n-heptane (30:70). The insoluble amine hydrochloride salts were removed by filtration. The filtrate was evaporated under reduced pressure to yield 14.0 g of 4-chloro-2-fluoro-5-nitrophenylisothiocyanate.

Workup

additionwas added dropwise to the mixture
additionAfter complete addition
temperatureto warm to room temperature
stirringstir for approximately 18 hours
customThe solvent was evaporated under reduced pressure
customleaving a residue
customThe insoluble amine hydrochloride salts were removed by filtration
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-484bcdc3f8a84eb6b7854448b3072b26
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04906281

Reaction notes

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