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

HRID 2059004

Reaction equation

HRID 2059004 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-10df2198bc5e4c8187b258816a5af1ba
Source dataset
uspto-grants-1982_03
Patent number
US04321202

Linked notes

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