Triethylamine → HCID 14551613, compound

HRID 1608041Notes

Reaction equation

HRID 1608041 reaction equation
[C:1](Cl)(Cl)=[S:2].[Cl:5][C:6]1[C:12]([NH:13][S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:11][C:9]([NH2:10])=[C:8]([F:19])[CH:7]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:5][C:6]1[C:12]([NH:13][S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:11][C:9]([N:10]=[C:1]=[S:2])=[C:8]([F:19])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 14551612HCID 14551612, compound

Product 1

HCID 14551613HCID 14551613, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a dry nitrogen atmosphere 0.84 ml (0.011 mole) of thiophosgene was added to a stirred solution of 2.8 g (0.011 mole) of 4-chloro-2-fluoro-5-(N-ethylsulfonylamino)aniline in 250 ml of chloroform. To this mixture was added dropwise 1.6 g (0.012 mole) of triethylamine. The resultant mixture was stirred at room temperature for approximately 18 hours. The solvent was removed from the mixture by evaporation under reduced pressure leaving an oily residue. This residue was purified by column chromatography on silica gel, eluting with methylene chloride/hexane (60/40) followed by methylene chloride, to yield 1.6 g of 4-chloro-5-(N-ethylsulfonylamino)-2-fluorophenyl isothiocyanate as a solid, m.p. 104°-105° C.

Workup

  1. customThe solvent was removed from the mixture by evaporation under reduced pressure
  2. customleaving an oily residue
  3. customThis residue was purified by column chromatography on silica gel
  4. washeluting with methylene chloride/hexane (60/40)

Sources & evidence

ORD record
ord-1cb3ed13b79a4e6695a7db2b5c8e4701
Source dataset
uspto-grants-1989_09
Patent number
US04868321

Reaction notes

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