((2-Chloroethyl)sulphonyl)benzene → HCID 20277899, compound

HRID 1248434Notes

Reaction equation

HRID 1248434 reaction equation
[CH2:1]([NH2:5])[C:2](=[CH2:4])[CH3:3].Cl[CH2:7][CH2:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:12]1([S:9]([CH2:8][CH2:7][NH:5][CH2:1][C:2](=[CH2:3])[CH3:4])(=[O:11])=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 761412-Methylallylamine

Product 1

HCID 20277899HCID 20277899, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of methallylamine (8.0 g; 1.12 mol), in toluene (20 ml) was added dropwise to a solution of 1-chloro-2-phenylsulphonylethane (11.54 g; 56.4 mmol) in toluene (100 ml) at 0° C. When the addition was complete the reaction mixture was allowed to warm to room temperature and stirred for 1 hr. Thin layer chromatography indicated that all of the starting material had been consumed. Ether (150 ml) was added and the precipitate filtered off. Removal of the solvent from the filtrate produced a colourless oil which was subjected to silica gel column chromatography using ethyl acetate as eluent. Fractions containing the component Rf=0.37 (ethyl acetate) were combined and evaporated to give the title amine as a colourless oil, in 75% yield.

Workup

  1. additionWhen the addition
  2. customhad been consumed
  3. additionEther (150 ml) was added
  4. filtrationthe precipitate filtered off
  5. customRemoval of the solvent from the filtrate
  6. customproduced a colourless oil which
  7. customevaporated

Sources & evidence

ORD record
ord-a41b0848f9f64eefbf06f711c7d7e2cf
Source dataset
uspto-grants-1985_06
Patent number
US04524073

Reaction notes

Loading…