Dimethylamine → N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

HRID 477299

Reaction equation

HRID 477299 reaction equation
[CH3:1][NH:2][CH3:3].[F:4][B-:5]([F:8])([F:7])[F:6].C(O[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=[N+:15]([CH3:17])[CH3:16])C.C(OCC)C>C(Cl)Cl>[F:4][B-:5]([F:8])([F:7])[F:6].[CH3:1][N:2]([CH3:3])[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:14]=[N+:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 3283Diethyl EtherHCID 86743577N-(3-ethoxy-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 86743575N-(dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethylamine (233 cc) in methylene chloride is added in the course of 1 hour 20 minutes, at a temperature of approximately 20° C., to a solution of N-(3-ethoxy-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (1,007 g) in methylene chloride. Anhydrous ethyl ether (2,000 cc) is then run slowly into the reaction medium, and the crystalline product is then separated off by filtration and dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of approximately 20° C. N-(3-Dimethylamino-3-ethoxycarbonylpropenylidene)-N-methylmethanaminium tetrafluoroborate (925 g), m.p. 102° C., is thereby obtained.

Workup

  1. customthe crystalline product is then separated off by filtration
  2. customdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of approximately 20° C

Sources & evidence

ORD record
ord-6c30ed02d468450493491dda1e297617
Source dataset
uspto-grants-1989_12
Patent number
US04886835

Linked notes

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