Process for making phosphonothioureides

Abstract

Abstract 1. A PROCESS FOR PREPARING A DESIRED COMPOUND OF THE FORMULA 1-(R-NH-C(=Y)-NH-),2-((R''-O)2-P(=O)-NH-C(=S)-NH-),X- BENZENE WHEREIN IN EACH OF THE FORMULAS OF THIS CLAIM, Y IS O OR S; R IS LOWER ALKYL SULFONYL, BENZENESULFONNYL, SUBSTITUTED BENZENESULFONYL WHEREIN THE SUBSTITUENTS ARE SELECTED FROM LOWER ALKYL, NITRO, HALO, LOWER ALKOXY, HALOLOWER ALKYL, DIALKYLAMINO, OR A TRIMETHYLENE GROUP BONDED TO THE 3,4-ADJACENT CARBONS, LOWER ACYL, BENZOYL OR SUBSTITUTED BENZOYL WHEREIN THE SUBSTITUENTS ARE SELECTED FROM LOWER ALKYL, NITRO, HALO, LOWER ALKOXY, HALO-LOWER ALKYL, DIALKYLAMINO OR CCL3. R'' IS LOWER ALKYL, LOWER ALKOXYALKYL, HALO-LOWER ALKYL, PHENYL OR SUBSTITUTED PHENYL HWEREIN THE SUBSTITUENTS ARE SELECTED FROM THE LOWER ALKYL, NITRO HALO, LOWER ALKOXY, HALO-LOWER ALKYL OR DIALKYLAMINO; AND X REPRESENTS FROM ONE TO FOUR SUBSTITUENTS WHICH MAY INDEPENDENTLY BE HYDROGEN, LOWER ALKY, LOWER ALKOXY OR HALOGEN; STEP 1-BRINGING TOGETHER IN AN INERT, WATER-FREE ORGANIC SOLVENT BOILING AT LEAST 30*C. AND IN WHICH THE ORGANIC REAGENTS OF SAID PROCESS ARE SOLUBLE, SUBSTANTIALLY EQUIMOLAR AMOUNTS OF THE FOLLOWING: (A) THE THIOCYANATE SALT OF A CATION HAVING A WATER-SOLUBLE CHLORIDE AND (B) A CHLOROPHOSPHATE HAVING THE FORMULA CL-P(=O)(-O-R'')2 AND PERMITTING THEM TO REACT AT A TEMPERATURE BETWEEN ABOUT 10* AND 90*C FOR AT LEAST ABOUT ONEHALF HOUR WITH AGITATION, WHEREBY THE FOLLOWING INTERMEDIATE IS FORMED; 8C) THE PHOSPHONOISOTHIACYANATE HAVING THE FORMULA S=C=N-P(PR'')2; STEP 2-ADDING TO THE REACTION MIXTURE RESULTING FROM STEP 1 THE FOLLOWING* (D) THE DI-AMINO BENZENE COMPOUND HAVING THE FORMULA 1,2-DI(H2N-),X-BENZENE IN AN AMOUNT WHICH IS SUBSTANTIALLY EQUIMOLR WITH SAID PHOSPHONOISOTHIOCYANATE (C) AND PERMITTING IT TO RECT AT A TEMPERATURE BELOW ABOUT 50*C FOR AT LEAST ABOUT TEN MINUTES WITH AGITATION, WHEREBY THE FOLLOWING INTERMEDIATE IS FORMED: (E) THE BENZENE COMPOND HAVING THE FORMULA 1-(H2N-),2-((R''-O)2-P(=O)-NH-C(=S)-NH-),X-BENZENE STEP 3- ADDING TO THE REACTION MIXTURE RESULTING FROM STEP 2 THE FOLLOWING: (F) THE ISOCYANATE OR ISOTHIOCYANATE HAVING THE FORMULA R-N=C=Y IN AN AMOUNT WHICH IS AT LEAST SUBSTANTIALLY EQUIMOLAR WITH SAID BENZENE COMPOUND (E) AND PERMITTING IT TO REACT AT A TEMPERATURE BETWEEN ABOUT 10* AND 80*C, FOR AT LEAST ABOUT TEN MINUTES WITH AGITTION, WHEREBY SAID DESIRED COMPOUND IS FORMED; AND STEP 4- SEPARATING SAID DESIRED COMPOUND FROM THE REACTION MIXTURE.

Inventors

• 👤 W Weir

Bibliographic Details