N-Methyl-4-nitroaniline → N-Methyl-N-(4-nitrophenyl)phosphoramidic dichloride

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Reaction Steps

p-Nitro-N-methylaniline (9.3 g, 0.061 mol) and 9 mL (0.1 mol) POCl3 were heated in 50 mL toluene to 90°-95° C. overnight. The solution was cooled and filtered. The volatiles were removed from the filtrate, giving 15.3 g of a purple, viscous oil. NMR (CDCl3): AA'XX' quartet from δ7.45-7.35 (4H), 3.37 (d,3H, J=14-15 Hz). No N--H was observed in the NMR. Due to an expected very high boiling point, this material was not distilled but used directly in the preparation of N-Methyl-N-(4-nitrophenyl) phosphoric triamide in the following Example VI.

Provenance & Evidence