Ethylenediamine → p-Toluenesulfonic acid

HRID 2116426Notes

Reaction equation

HRID 2116426 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC1C(C)=C(C)C(C)=C(C)C=1.C(N)CN>ClCCl>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 12784PentamethylbenzeneHCID 521998p-Toluenesulfonic acid monohydrate2×

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of p-toluenesulfonic acid monohydrate (TsOH) (7.5 mg, 39.4 μmol) and of pentamethylbenzene (6.6 mg, 44.5 μmol, internal standard) in solution in dichloromethane (300 μl) was treated with 3 equivalents of polyimine prepared according to example 1 (12 mg, 120 μmol). After filtering and evaporating, it was observed, by NMR, that the TsOH/pentamethylbenzene ratio was 0.02. Thus, only 0.89 μmol of TsOH remains in the medium, i.e. only 2% of the initial amount.

Workup

  1. customprepared
  2. filtrationAfter filtering
  3. customevaporating

Sources & evidence

ORD record
ord-020e5c3461ef4af9b64e8ff96bff3cac
Source dataset
uspto-grants-2008_10
Patent number
US07438818B2

Reaction notes

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