4-Chloroaniline → HCID 57426257, compound

HRID 1075744Notes

Reaction equation

HRID 1075744 reaction equation
[CH2:1]([S:3]([CH2:6][S:7]([CH2:10][CH3:11])(=[O:9])=[O:8])(=[O:5])=[O:4])[CH3:2].[CH:12]([O-])([O-])OCC.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C(O)C>[CH2:10]([S:7]([C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:12][NH:23][C:22]1[CH:24]=[CH:25][C:19]([Cl:18])=[CH:20][CH:21]=1)(=[O:9])=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 240593bis(ethylsulfonyl)methane2×HCID 53630039Ethylorthoformate

Product 1

HCID 57426257HCID 57426257, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ten grams (0.05 mole) of bis(ethylsulfonyl)methane, prepared by the procedure described in Cronyl "Sulfones. I. Methods for the Preparation of Certain Alkanes, Alkenes, Acids and Lactones with Bis-(ethylsulfonyl)-methane" in J. Am. Chem. Soc., vol. 74, page 1225 (see p. 1228), published 1952, was mixed with 7.4 grams (0.05 mole) of ethyl orthoformate and 6.4 grams (0.05 mole) of p-chloroaniline and the mixture was heated at 95°-145°C. (pot) during which time about 7 milliliters of ethanol distilled off. The reaction mixture was then further heated at 150°-160°C. for 1 hour and then cooled. The solid reaction product was then washed with cold ethanol, and recrystallized from ethanol to give 7.3 grams of 2,2-bis(ethylsulfonyl)vinyl-4-chloroaniline, melting point 173°-175°C. having the structural formula ##SPC5##

Workup

  1. distillationdistilled off
  2. temperatureThe reaction mixture was then further heated at 150°-160°C. for 1 hour
  3. temperaturecooled
  4. customThe solid reaction product
  5. washwas then washed with cold ethanol
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f795a0007d164e4592cb1a42cd52c86e
Source dataset
uspto-grants-1976_05
Patent number
US03954707

Reaction notes

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