Dimethylamine → HCID 19373598, compound

HRID 2052610Notes

Reaction equation

HRID 2052610 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH3:18][NH:19][CH3:20].[CH2:21]=O>CO>[CH3:18][N:19]([CH2:21][C:13]1[C:14]([O:16][CH3:17])=[CH:15][C:2]([OH:1])=[C:3]([CH:12]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:20]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 46322-Hydroxy-4-methoxybenzophenone

Product 1

HCID 19373598HCID 19373598, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

228.3 g (1.0 mole) of 2-hydroxy-4-methoxy-benzophenone, 146.3 (1.3 moles, 40% aqueous solution) of dimethylamine, 105.4 g (1.3 moles, 37% aqueous solution) of formalin and 1200 ml of methanol was put into a flask, dissolved and heated under stirring at reflux temperature (68° to 70° C.) for 6 hours. When solvent was vacuum distilled off, 285 gr of 5-dimethylaminomethyl-2-hydroxy-4-methoxybenzophenone was obtained. The product had m.p. 69° C., infrared absorption at 1620 (Carbonyl), 2760 and 2800 (N--CH group) wave numbers, and neutralization equivalent (as nitrogen) 4.89% (Calculated 4.91%). The NMR spectrum provided evidence for the 5-position of the dimethylaminomethyl group.

Workup

  1. dissolutiondissolved
  2. temperatureheated
  3. temperatureat reflux temperature (68° to 70° C.) for 6 hours
  4. distillationdistilled off

Sources & evidence

ORD record
ord-e1c22212da2449ef872b6d8d4fd5ec32
Source dataset
uspto-grants-1980_01
Patent number
US04186151

Reaction notes

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