N,N,N′,N′-Tetramethylformamidinium chloride

[6] For drying, the salt is dissolved in dichloromethane and the solution is treated with solid anhydrous sodium sulfate.

After several dissolutions in dichloromethane and acetone, and precipitations with tetrahydrofuran, a colorless solid is obtained, which is stable under air and moisture sealing.

Therefore, also syntheses of the much better processible salts N,N,N′,N′-tetramethylformamidinium methylsulfate[6] (from the dimethylformamide–dimethylsulfate complex[8]) and of N,N,N′,N′-tetramethylformamidinium p-toluenesulfonate (from dimethylformamide and p-toluenesulfonyl chloride) were investigated.

From N,N,N′,N′-tetramethylformamidinium chloride and sodium ethoxide in ethanol, dimethylformamide diethyl acetal is formed in 68% yield.

[18] Strong bases (such as phenyllithium) can abstract a proton from the formamidinium cation of N,N,N′,N′-tetramethylformamidinium forming bis(dimethylamino)carbene.

Synthesis of N,N,N′,N′-tetramethylformamidinium chloride with thionyl chloride
Synthesis of N , N , N ′, N ′-tetramethylformamidinium chloride with thionyl chloride
Mesomerism of N,N,N′,N′-tetramethylformamidinium chloride
Mesomerism of N , N , N ′, N ′-tetramethylformamidinium chloride
Reaction of N,N,N′,N′-tetramethylformamidinium chloride with germanium(II) chloride
Reaction of N , N , N ′, N ′-tetramethylformamidinium chloride with germanium(II) chloride
Aminomethylenation with N,N,N′,N′-tetramethylformamidinium chloride
Aminomethylenation with N , N , N ′, N ′-tetramethylformamidinium chloride
Synthesis of tris(dimethylamino)methane
Synthesis of tris(dimethylamino)methane
Synthesis of dimethylformamide diethyl acetal
Synthesis of dimethylformamide diethyl acetal
Synthesis of bis(dimethylamino)acetonitrile
Synthesis of bis(dimethylamino)acetonitrile
Synthesis of dimethylaminomalonic acid dinitrile
Synthesis of dimethylaminomalonic acid dinitrile
Transamination of N,N,N′,N′-tetramethylformamidinium chloride
Transamination of N , N , N ′, N ′-tetramethylformamidinium chloride
Formation of bis(dimethylamino)carbene from N,N,N′,N′-tetramethylformamidinium chloride
Formation of bis(dimethylamino)carbene from N , N , N ′, N ′-tetramethylformamidinium chloride