N,N-disubstituted derivatives of 3-carboxamide or 3-thiocarboxamide-7-(3-chloro-2-propenyl)-1,3,5,7-tetraazabicyclo(3.3.1) nonane and preparation II
AssigneeThe Dow Chemical Company
InventorsAlbertha M. Paul, Charles E. Moppett
Life of this patent
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Abstract
Compounds of the formula ##STR1## where X represents O or S and R.sub.1 and R.sub.2 each represents lower alkyl, phenyl or (lower alkyl)phenyl. The compounds are prepared by reacting the ring-opened intermediate (obtained by reacting cis-1-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1.sup.3,7) decane chloride with excess aqueous sodium hydroxide) with an equivalent amount of a corresponding carbamoyl halide or thiocarbamoyl halide or at a low temperature to give the indicated tetrasubstituted urea or thiourea product. The compounds have antimicrobial utility.
Claims7
A compound corresponding to the formula ##STR5## wheren X represents O or S and R.sub.1 and R.sub.2 each represents lower alkyl, phenyl or (lower alkyl)phenyl.
Method for making an N,N-disubstituted derivative of 3-carboxamide- or 3-thiocarboxamide-7-cis-(3-chloro-2-propenyl)-1,3,5,7-tetraazabicyclo-(3.3 .1)nonane by mixing together at about 0.degree. C until reaction is substantially complete substantially equivalent proportions of (1) a carbamoyl or thiocarbamoyl halide having the formula hal-C=X(NR.sub.1 R.sub.2) wherein hal is Cl or Br, X is O or S and R.sub.1 and R.sub.2 each is lower alkyl, phenyl or (lower alkyl)phenyl dissolved in an organic non-nucleophilic solvent and (2) the reaction product of Dowicil.sup.(R) 200 with excess aqueous sodium hydroxide at a reaction temperature between about minus 15.degree. and about 5.degree. C, also in solution in a similar solvent, in the presence of an acid acceptor, and recovering the said product.
Dependencies are inferred from the claim text.