dimethylaminomethylidene(dimethyl)azanium;methyl sulfate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N,N′,N′-tetramethylformamidinium methylsulfate (3 g) is added to water (25 ml) and the resulting mixture is cooled to 0° C. This mixture is then added to a cooled solution of ammonium hexafluorophosphate (4.6 g) in water (25 ml). The so formed precipitate is then collected by filtration. The precipitate is washed with cold water (2×10 ml) and then with diethyl ether (10 ml). Drying in vacuo gives N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (18, R6=Me, R7=Me) as a white solid. 1H NMR (DMSO-d6), 7.90 (1H), 3.26 (6H), 3.14 (6H). The so formed precipitate is then collected by filtration The precipitate is washed with cold water (2×10 ml) Drying in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N.N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR (C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H). at reflux for 1 h The reaction mixture is cooled to room temperature the phases are separated The lower layer is washed three times with anhydrous tert-butyl methyl ether

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N.N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR (C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H). at reflux for 1 h The reaction mixture is cooled to room temperature the phases are separated The lower layer is washed three times with anhydrous tert-butyl methyl ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N,N′,N′-tetramethylformamidinium methylsulfate (3 g) is added to water (25 ml) and the resulting mixture is cooled to 0° C. This mixture is then added to a cooled solution of ammonium hexafluorophosphate (4.6 g) in water (25 ml). The so formed precipitate is then collected by filtration. The precipitate is washed with cold water (2×10 ml) and then with diethyl ether (10 ml). Drying in vacuo gives N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (18, R6=Me, R7=Me) as a white solid. 1H NMR (DMSO-d6), 7.90 (1H), 3.26 (6H), 3.14 (6H). The so formed precipitate is then collected by filtration The precipitate is washed with cold water (2×10 ml) Drying in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N,N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR (C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H). at reflux for 1 h The reaction mixture is cooled to room temperature the phases are separated The lower layer is washed three times with anhydrous tert-butyl methyl ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N,N′,N′-tetramethylformamidinium methylsulfate (3 g) is added to water (25 ml) and the resulting mixture is cooled to 0° C. This mixture is then added to a cooled solution of ammonium hexafluorophosphate (4.6 g) in water (25 ml). The so formed precipitate is then collected by filtration. The precipitate is washed with cold water (2×10 ml) and then with diethyl ether (10 ml). Drying in vacuo gives N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (18, R6=Me, R7=Me) as a white solid. 1H NMR (DMSO-d6), 7.90 (1H), 3.26 (6H), 3.14 (6H). The so formed precipitate is then collected by filtration The precipitate is washed with cold water (2×10 ml) Drying in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N,N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR(C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H). at reflux for 1 h The reaction mixture is cooled to room temperature the phases are separated The lower layer is washed three times with anhydrous tert-butyl methyl ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N,N′,N′-tetramethylformamidinium methylsulfate (3 g) is added to water (25 ml) and the resulting mixture is cooled to 0° C. This mixture is then added to a cooled solution of ammonium hexafluorophosphate (4.6 g) in water (25 ml). The so formed precipitate is then collected by filtration. The precipitate is washed with cold water (2×10 ml) and then with diethyl ether (10 ml). Drying in vacuo gives N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (18, R6=Me, R7=Me) as a white solid. 1H NMR (DMSO-d6), 7.90 (1H), 3.26 (6H), 3.14 (6H). The so formed precipitate is then collected by filtration The precipitate is washed with cold water (2×10 ml) Drying in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N.N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR (C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H). at reflux for 1 h The reaction mixture is cooled to room temperature the phases are separated The lower layer is washed three times with anhydrous tert-butyl methyl ether

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N,N,N′,N′-tetramethylformamidinium methylsulfate (3 g) is added to water (25 ml) and the resulting mixture is cooled to 0° C. This mixture is then added to a cooled solution of ammonium hexafluorophosphate (4.6 g) in water (25 ml). The so formed precipitate is then collected by filtration. The precipitate is washed with cold water (2×10 ml) and then with diethyl ether (10 ml). Drying in vacuo gives N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (18, R6=Me, R7=Me) as a white solid. 1H NMR (DMSO-d6), 7.90 (1H), 3.26 (6H), 3.14 (6H). The so formed precipitate is then collected by filtration The precipitate is washed with cold water (2×10 ml) Drying in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of N.N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR (C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H). at reflux for 1 h The reaction mixture is cooled to room temperature the phases are separated The lower layer is washed three times with anhydrous tert-butyl methyl ether