Water → HCID 20394040, compound

HRID 26958Notes

Reaction equation

HRID 26958 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[N:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 29959682-[3-(Dimethylamino)propoxy]benzaldehyde

Product 1

HCID 20394040HCID 20394040, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 32.5 g (0.156 mole) of 2-(3-dimethylaminopropoxy)benzaldehyde and 14.6 g (0.157 mole) of aniline in 150 ml of toluene is refluxed for 9 hours. Water which is formed very slowly is collected in a Dean-Stark trap. The bulk of solvent is removed on a rotary evaporator and the oily residue is fractionated to give 20.0 g of product; boiling point 165°-170° C./0.2 mm of Hg.

Workup

  1. customis collected in a Dean-Stark trap
  2. customThe bulk of solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-6ce00da627874f9b8fb7645883f89f6c
Source dataset
uspto-grants-1979_04
Patent number
US04151354

Reaction notes

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