Some Reactions of N, N-Dimethylformamide Dimethylacetal

Abstract

Aryl magnesium bromides were treated with N, N-dimethylformamide dimethylacetal (DMFDA) in tetrahydrofuran to obtain the corresponding 1, 1-diaryltrimethylamines.
2ArMgBr+CH₃_??_CH₃_??_N-CH_??_OCH₃_??_OCH₃→CH₃_??_CH₃_??_N-CH_??_Ar_??_Ar
Ar = C₆H₅, p-CF₃OC₆H₄, o-CH₃OC₆H₄, p-CH₃C₆H₄, m-CH₃C₆H₄, o-CH₃C₆H₄
N'-Arylarylamidines reacted with an exess amount of DMFDA to afford the corresponding N-dimethylaminomethylideneamidines, as follows :
ArC_??_NH₂_??_NAr'+CH₃_??_CH₃_??_N-CH_??_OCH₃_??_OCH₃→ArC_??_N=CH-N_??_CH₃_??_CH₃_??_NAr'
Ar =p-CH₃C₆H₄ Ar' C₆H₅, Ar C₆H₅ Ar' C₆H₅, Ar = 2-C₁₀H₇ Ar' = C₆H₅, Ar =p-ClC₆H₄ Ar' = C₆H₅, Ar C₆H₅ Ar' =p-ClC₆H₄
Condensation reactions of o-aminobenzamide and o-aminobenzenesulfamide with DMFDA or ethyl orthoformate yielded 4-keto-3, 4-dihydroquinazoline and 2H-1, 2, 4-benzothiadiazine 1, 1-dioxide, respectively.