p-Toluidine → Dimethyl-p-toluidine

HRID 2286825Notes

Reaction equation

HRID 2286825 reaction equation
N[C:2]1C=CC(C)=CC=1.O=P(Cl)(Cl)Cl.[CH3:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1>CO>[CH3:14][N:15]([CH3:2])[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7813p-Toluidine2×HCID 12165Benzenamine, N,4-dimethyl-HCID 24813Phosphorus oxychloride

Product 1

HCID 7471Dimethyl-p-toluidineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
280 °C

Procedure

A mixture of 749 g of p-toluidine, 1,008 g of methanol and 7.9 g of POCl3 is introduced into a 3 l autoclave with an up-and-down stirrer. After closing the autoclave, it is heated up to 280° C. and kept at this temperature for about 3 hours. A pressure of about 60 bar is thereby established. A crude oil composed of <1% of p-toluidine, 1% of N-methyl-p-toluidine and 94% of N,N-dimethyl-p-toluidine is obtained.

Workup

  1. additionis introduced into a 3 l autoclave with an up-and-down stirrer

Sources & evidence

ORD record
ord-8d20bdb187814a7bb0e3e2e96200a502
Source dataset
uspto-grants-1981_05
Patent number
US04268458

Reaction notes

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