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

HRID 1719099Notes

Reaction equation

HRID 1719099 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([NH:8][CH3:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:12]=[P:13](Cl)([Cl:15])[Cl:14]>C1(C)C=CC=CC=1>[CH3:9][N:8]([C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[P:13]([Cl:15])([Cl:14])=[O:12]

Participants

4

Reactant 2

HCID 7483N-Methyl-4-nitroanilineHCID 24813Phosphorus oxychloride

Product 1

HCID 54046321N-Methyl-N-(4-nitrophenyl)phosphoramidic dichloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered
  3. customThe volatiles were removed from the filtrate
  4. customgiving 15.3 g of a purple, viscous oil
  5. distillationthis material was not distilled
  6. customused directly in the preparation of N-Methyl-N-(4-nitrophenyl) phosphoric triamide in the following Example VI

Sources & evidence

ORD record
ord-aa09c776236f4a25b114408fbde4f5fb
Source dataset
uspto-grants-1985_09
Patent number
US04539037

Reaction notes

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