N-Methylaniline → HCID 23412846, compound

HRID 1719098Notes

Reaction equation

HRID 1719098 reaction equation
[O:1]=[P:2]([Cl:5])(Cl)[Cl:3].[CH3:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH3:6][N:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[P:2]([Cl:5])([Cl:3])=[O:1]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 24813Phosphorus oxychloride

Product 1

HCID 23412846HCID 23412846, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 500 mL three-necked flask was fitted with an N2 inlet, thermometer and dropping funnel. The flask was flushed with nitrogen and charged with 150 mL dry ether and 31.1 g (0.203 mol) POCl3. In the dropping funnel was placed a solution of 21.4 g (0.20 mol) N-methylaniline in 5 mL ether. The amine solution was added to the solution of POCL3 (at -12° to -17° C.) over 40 minutes. The temperature was allowed to rise slowly to room temperature and stirring continued for 2 h thereafter. After filtering, volatiles were removed from the filtrate at reduced pressure. The 15.4 g (69% yield) of crude product was distilled (bp 96°-98° C. at 0.05 mm).

Workup

  1. customA 500 mL three-necked flask was fitted with an N2 inlet
  2. customThe flask was flushed with nitrogen
  3. customto rise slowly to room temperature
  4. filtrationAfter filtering
  5. customvolatiles were removed from the filtrate at reduced pressure

Sources & evidence

ORD record
ord-65759d297d5043ef82e679c73399de43
Source dataset
uspto-grants-1985_09
Patent number
US04539037

Reaction notes

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