Dimethylamine → N,N-Dimethyl-N'-phenyl-benzamidine

HRID 544247

Reaction equation

HRID 544247 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:20][NH:21][CH3:22]>C(Cl)Cl>[CH3:20][N:21]([CH3:22])[C:1](=[N:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 7168BenzanilideHCID 24386Thionyl Chloride

Product 1

HCID 351862N,N-Dimethyl-N'-phenyl-benzamidineYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a slurry of 19.7 g of benzanilide (m.p. 162°-164° C.) in 200 ml of methylene chloride was added a solution of 12.0 g of thionylchloride in 50 ml of methylene chloride. After the addition was completed and the reaction mixture was stirred for one hour at room temperature, gaseous dimethylamine was introduced until the solution became saturated. Workup by filtration, waterwash, removal of the solvent and distillation afforded N,N-dimethyl-N'-phenylbenzamidine in 18.6 g or 83% yield.

Workup

  1. additionAfter the addition
  2. filtrationWorkup by filtration, waterwash, removal of the solvent and distillation

Sources & evidence

ORD record
ord-7f7c2afd18b74a8db7d15719a450e9da
Source dataset
uspto-grants-1984_05
Patent number
US04448975

Linked notes

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