N,N-Dimethylaniline → 2-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

HRID 434800Notes

Reaction equation

HRID 434800 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.NC(N)=O.[CH3:16][N:17]([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:25][N:26]([CH3:36])[C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([OH:32])=[O:31].S(=O)(=O)(O)O>O>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]([C:21]2[CH:22]=[CH:23][C:18]([N:17]([CH3:24])[CH3:16])=[CH:19][CH:20]=2)[C:33]2[CH:34]=[CH:35][C:27]([N:26]([CH3:36])[CH3:25])=[CH:28][C:29]=2[C:30]([OH:32])=[O:31])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 949N,N-DimethylanilineHCID 1118Sulfuric AcidHCID 1176UreaHCID 74794-(Dimethylamino)BenzaldehydeHCID 668373-(Dimethylamino)benzoic acid

Product 1

HCID 1020632-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acidYield 9.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 38.0 ml of water, 17.4 g (0.1 mole) of 85.5 percent 4-dimethylaminobenzaldehyde, 6.0 g (0.1 mole) of urea, 12.6 g (0.1 mole) of N,N-dimethylaniline, 18.2 g (0.11 mole) of 3-dimethylaminobenzoic acid and 14.6 ml (0.273 mole) of concentrated sulfuric acid was maintained at a temperature in the range of 90° to 95° C. for approximately two and one-half hours with stirring. Slowly, 240.0 ml of water was added to the reaction mixture and the resulting mixture was stirred for approximately eight hours. The mixture was filtered to remove the insolubles and the filtrate was added with stirring to a solution of 30.0 ml of concentrated ammonium hydroxide dissolved in 150.0 ml of water. The pH of the resultant mixture was adjusted to 11.0 by gradually adding 21.6 g of 90 percent potassium hydroxide. After stirring approximately one-half hour, the mixture was filtered retaining both the filtercake and the filtrate. The filtrate was adjusted to a pH of approximately 4.8 by slowly adding glacial acetic acid. The solid which formed was collected by filtration, washed with water and dried in vacuo to obtain 4.1 g of 2-[bis(4-dimethylaminophenyl)]methyl-5-dimethylaminobenzoic acid (Formula II: Y=4--N(CH3)2 ; R=R1 =R2 =R3 =CH3), a solid.

Workup

  1. temperaturewas maintained at a temperature in the range of 90° to 95° C. for approximately two and one-half hours
  2. stirringthe resulting mixture was stirred for approximately eight hours
  3. filtrationThe mixture was filtered
  4. customto remove the insolubles
  5. additionthe filtrate was added
  6. stirringwith stirring to a solution of 30.0 ml of concentrated ammonium hydroxide
  7. dissolutiondissolved in 150.0 ml of water
  8. additionby gradually adding 21.6 g of 90 percent potassium hydroxide
  9. stirringAfter stirring approximately one-half hour
  10. filtrationthe mixture was filtered
  11. customThe solid which formed
  12. filtrationwas collected by filtration
  13. washwashed with water
  14. customdried in vacuo

Sources & evidence

ORD record
ord-8d42c45540d64cbea15267c990a473c6
Source dataset
uspto-grants-1983_08
Patent number
US04399291

Reaction notes

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