HCID 11197435, compound → HCID 20084430, compound

HRID 1609271Notes

Reaction equation

HRID 1609271 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.Cl.[OH-].[Na+].CCOCC>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

7

Reactant 2

HCID 11197435HCID 11197435, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 20084430HCID 20084430, compoundYield 101.1%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

In 130 ml of ethanol was suspended 22.5 g of ethyl 2-(2-nitrophenylthio)benzoate and, then, a solution of 58.7 g of tin(IV) chloride dihydrate in a mixture of 70 ml of concentrated hydrochloric acid and 45 ml of ethanol was added en bloc. The mixture was stirred at room temperature for 3 hours, after which it was poured in a mixture of 600 ml of 10% aqueous sodium hydroxide solution and 500 ml of ether with cooling and stirring. The ether layer was separated, washed with water and saturated aqueous sodium chloride solution in that order and dried. Finally, the ether was distilled off to give 20.5 g of the title compound as a light yellow oil.

Workup

  1. additionwas added en bloc
  2. temperaturewith cooling
  3. stirringstirring
  4. customThe ether layer was separated
  5. washwashed with water and saturated aqueous sodium chloride solution in that order
  6. customdried
  7. distillationFinally, the ether was distilled off

Sources & evidence

ORD record
ord-d63a36ed8dc6417fb5e8c0b4589edcbb
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

Loading…