HCID 20461261, compound → HCID 20493217, compound

HRID 851527Notes

Reaction equation

HRID 851527 reaction equation
[F:1][S:2]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([C:10]1[S:14][C:13]([NH:15]C(OCC(Cl)(Cl)Cl)=O)=[C:12]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:11]=1)=[O:9])(=[O:4])=[O:3]>[Zn].C(O)(C)C>[NH2:15][C:13]1[S:14][C:10]([C:8](=[O:9])[C:7]2[CH:29]=[CH:30][CH:31]=[C:5]([S:2]([F:1])(=[O:3])=[O:4])[CH:6]=2)=[CH:11][C:12]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 1

HCID 20461261HCID 20461261, compound

Product 1

HCID 20493217HCID 20493217, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 175 g (0.33 mole) of ethyl 5-(m-fluorosulfonylbenzoyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-thenoate and 4200 ml of isopropyl alcohol was treated with 175 g of zinc dust at 75° to 77° C. over a 6-minute period. The mixture was held at gentle reflux for 50 minutes before a sudden onset of reaction, characterized by vigorous boiling of the solvent, was noticed. Heating was removed until the reaction subsided. Reflux was continued until all the urethane was consumed, as indicated by thin-layer chromatography in 30 percent acetone:70 percent hexane. The mixture was filtered hot through Celite (diatomaceous earth) and the filtrate was evaporated slowly in an evaporating dish until about one liter of solvent had been removed. The solid was collected by filtration to yield 66 g (56 percent) of yellow solid, melting point 170° to 172° C. A second crop was obtained by further evaporation (melting point 153° to 168° C.), and this was recrystallized from isopropyl alcohol to yield 14.5 g (12 percent) of yellow solid, melting point 168° to 170° C.

Workup

  1. temperatureat gentle reflux for 50 minutes before a sudden onset of reaction
  2. temperatureHeating
  3. customwas removed until the reaction
  4. temperatureReflux
  5. customwas consumed
  6. filtrationThe mixture was filtered hot through Celite (diatomaceous earth)
  7. customthe filtrate was evaporated slowly in an evaporating dish until about one liter of solvent
  8. customhad been removed
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-575ee85e3eb14c3bb142bfe7cfb45d16
Source dataset
uspto-grants-1983_05
Patent number
US04385104

Reaction notes

Loading…