Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-10-13
1994-07-26
Brust, Joseph Paul
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546 14, 549 4, 549 74, 549 75, 549214, 549491, 558351, 558408, 558430, 558432, 558433, 558434, 558452, 556417, C07C25316, C07C, C07C, C07D21357
Patent
active
053328256
ABSTRACT:
This invention relates to two processes for preparing aminoacetonitriles in one vessel under anhydrous conditions. Process I involves the steps of: (A) reacting trimethylsilyl cyanide and an aldehyde in a water miscible amide solvent to obtain a silyl blocked cyanohydrin solution; (B) adding a catalytic amount of water to the silyl blocked cyanohydrin solution from Step (A); and (C) passing ammonia through the solution to obtain an aminoacetonitrile. Process II involves the steps of: (A') reacting trimethylsilyl cyanide with an aldehyde in the absence of solvent to form a silyl blocked cyanohydrin; (B') adding a water miscible amide solvent to the silyl blocked cyanohydrin from Step (A') to obtain a solution; and (C') passing ammonia through the solution to obtain an aminoacetonitrile. Aminoacetonitriles are important intermediates in the preparation of amino acids, thiadiazoles, acylaminoacetonitriles, and imidazole derivatives.
REFERENCES:
patent: 4551526 (1985-11-01), Mai et al.
patent: 4611076 (1986-09-01), Dong et al.
patent: 4694103 (1987-09-01), Krepski et al.
patent: 5169973 (1992-12-01), Gibson et al.
"Facile Synthesis of .alpha.-Aminonitriles", Khuong Mai et al, Tetrahedron Letters vol. 25, No. 41, pp. 4583-4586, (1984).
"A Fast N-Substituted .alpha.-Aminonitrile Synthesis", Khuong Mai et al, Synthetic Communications 15 (2), 157-163 (1985).
Brust Joseph Paul
Eastman Kodak Company
Thallemer John D.
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