Phenyl chloroacetate → N-2-((Phenoxycarbonyl)oxy)ethyl-N-((phenoxycarbonyl)methyl)-N,N-dimethyl-ammonium Chloride

HRID 51992Notes

Reaction equation

HRID 51992 reaction equation
[O:1]([C:8]([O:10][CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16][CH2:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>C(#N)C>[Cl-:16].[O:1]([C:8]([O:10][CH2:11][CH2:12][N+:13]([CH2:17][C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])([CH3:15])[CH3:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12108Phenyl chloroacetateHCID 11117296Carbonic acid, 2-(dimethylamino)ethyl phenyl ester

Product 1

HCID 19962803N-2-((Phenoxycarbonyl)oxy)ethyl-N-((phenoxycarbonyl)methyl)-N,N-dimethyl-ammonium Chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 250 ml three-necked round-bottomed flask fitted with a reflux condenser, magnetic stirrer, internal thermometer, addition funnel, and argon inlet are added N-[2-((phenoxycarbonyl)oxy)ethyl]-N,N-dimethylamine (25.00 g, 0.120 mol), acetonitrile (100 ml), and phenyl chloroacetate (20.38 g, 0.120 mol) over 5 min. After addition is complete, the mixture is heated to reflux for 3 h. The cooled mixture is triturated with ether (500 ml). A white solid, 23.15 g (51%) is isolated to give 9.

Workup

  1. customTo a 250 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 3 h
  6. customThe cooled mixture is triturated with ether (500 ml)
  7. customA white solid, 23.15 g (51%) is isolated
  8. customto give 9

Sources & evidence

ORD record
ord-5aa905e6e57b49b59d89473150b79002
Source dataset
uspto-grants-1997_04
Patent number
US05616546

Reaction notes

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