Acetonitrile → N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N,N-dimethylammonium Methylsulfate

HRID 51988

Reaction equation

HRID 51988 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.[CH3:30][O:31][S:32]([O:35]C)(=[O:34])=[O:33]>CCOCC>[CH3:30][O:31][S:32]([O-:35])(=[O:34])=[O:33].[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 6497Dimethyl SulfateHCID 19962809N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine

Product 1

HCID 19962810N,N-Bis[2-((phenoxycarbonyl)oxy)ethyl]-N,N-dimethylammonium Methylsulfate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 1000 ml three-necked round-bottomed flask fitted with a reflux condenser, magnetic stirrer, internal thermometer, addition funnel, and argon inlet are added N,N-bis[2-((phenoxycarbonyl)oxy)ethyl]-N-methylamine (100.00 g, 0.278 mol), acetonitrile (270 ml), and dimethylsulfate (35.93 g, 0.278 mol) over 10 min. 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 after approximately 15 min to give 4 as a white powder, 126.26 g (93%): mp 85°-87° C.

Workup

  1. customTo a 1000 ml three-necked round-bottomed flask fitted with a reflux condenser, magnetic stirrer
  2. additioninternal thermometer, addition funnel, and argon inlet
  3. additionAfter addition
  4. temperaturethe mixture is heated
  5. temperatureto reflux for 2 h
  6. customThe product precipitates from the mixture after approximately 15 min

Sources & evidence

ORD record
ord-02cacc73113c408c9974ae03a4320444
Source dataset
uspto-grants-1997_04
Patent number
US05616546

Linked notes

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