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

HRID 1074092Notes

Reaction equation

HRID 1074092 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N:7](C)[C:8](C1C=CC=CC=1)=CC=[N+](C)C.[CH3:21][N:22]([CH3:35])[CH:23]=[CH:24][C:25](=O)[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:27].F[B-](F)(F)F.C([O+](CC)CC)C.CNC>ClCCl>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N:7]([CH3:8])[C:25]([C:26](=[O:27])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:24][CH:23]=[N+:22]([CH3:35])[CH3:21]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 2723982Triethyloxonium tetrafluoroborateHCID 545728964-Dimethylamino-1-phenyl-3-butene-1,2-dioneHCID 75556698N-(3-dimethylamino-3-phenylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Product 1

HCID 86743604N-(3-dimethylamino-3-benzoylpropenylidene)-N-methylmethanaminium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure is as in Example 24 for the preparation of N-(3-dimethylamino-3-phenylpropenylidene)-N-methylmethanaminium tetrafluoroborate, starting with 4-dimethylamino-1-phenyl-3-butene-1,2-dione (9.3 g), triethyloxonium tetrafluoroborate (10.3 g) and dimethylamine (3.2 cc) in dichloromethane (140 cc). After precipitation in ethyl acetate (30 cc), N-(3-dimethylamino-3-benzoylpropenylidene)-N-methylmethanaminium tetrafluoroborate (5 g), m.p. 140° C., is obtained.

Workup

  1. customAfter precipitation in ethyl acetate (30 cc)

Sources & evidence

ORD record
ord-787f4eb0dfb442cea39374579af14eba
Source dataset
uspto-grants-1990_11
Patent number
US04971979

Reaction notes

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