Acetonitrile → N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N,N-dimethylammonium p-Toluene-sulfonate

HRID 234602Notes

Reaction equation

HRID 234602 reaction equation
[O:1]([C:8]([O:10][CH2:11][CH2:12][N:13]([CH2:15][CH2:16][O:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[CH3:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](#N)C.[C:30]1([CH3:41])[CH:35]=[CH:34][C:33]([S:36]([O:39]C)(=[O:38])=[O:37])=[CH:32][CH:31]=1>CCOCC>[C:30]1([CH3:41])[CH:31]=[CH:32][C:33]([S:36]([O-:39])(=[O:37])=[O:38])=[CH:34][CH:35]=1.[O:1]([C:8]([O:10][CH2:11][CH2:12][N+:13]([CH2:15][CH2:16][O:17][C:18]([O:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:19])([CH3:27])[CH3:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6645Methyl p-toluenesulfonateHCID 19962809N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine

Product 1

HCID 19962811N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N,N-dimethylammonium p-Toluene-sulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 250 ml round-bottomed flask fitted with a reflux condenser, magnetic stirrer, and argon inlet are added N,N-bis[2((phenoxycarbonyl)oxy)ethyl]-N-methylamine (25.00 g, 69.6 mmol), acetonitrile (100 ml), and methyl p-toluenesulfonate (12.95 g, 69.6 mmol). After addition is complete, the mixture is heated to reflux for 2 h. The cooled mixture is treated with ether (500 ml). The product precipitates from the mixture and dried to give 5 as a white powder, 31.14 g (81%): mp 117°-118° C.

Workup

  1. customTo a 250 ml round-bottomed flask fitted with a reflux condenser, magnetic stirrer, and argon inlet
  2. additionAfter addition
  3. temperaturethe mixture is heated
  4. temperatureto reflux for 2 h
  5. customThe product precipitates from the mixture
  6. customdried

Sources & evidence

ORD record
ord-f9458d1077c043beb177ab0ffce4a753
Source dataset
uspto-grants-1997_01
Patent number
US05595967

Reaction notes

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