Water → N-[2,4-Diisopropyl-5-methoxymethyl-benzal]-phenylamine

HRID 846882Notes

Reaction equation

HRID 846882 reaction equation
[CH:1]([C:4]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[C:9]([CH2:15][O:16][CH2:17]C)=[CH:8][C:5]=1[CH:6]=O)([CH3:3])[CH3:2].[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([C:4]1[CH:11]=[C:10]([CH:12]([CH3:13])[CH3:14])[C:9]([CH2:15][O:16][CH3:17])=[CH:8][C:5]=1[CH:6]=[N:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 198843442,4-Diisopropyl-5-ethoxymethyl-benzaldehyde

Product 1

HCID 14850549N-[2,4-Diisopropyl-5-methoxymethyl-benzal]-phenylamine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 10.36 g (44.3 mmol) of the compound from Example 5, 4.06 g (44.6 mmol) of freshly distilled aniline and 0.3 g of p-toluenesulphonic acid in 370 ml of toluene is heated under reflux for 1.5 h in a water separator (molecular sieve 4 Å), diluted with ethyl acetate after cooling to room temperature, washed with saturated sodium hydrogencarbonate solution and water, dried using sodium sulphate and concentrated in vacuo.

Workup

  1. washwashed with saturated sodium hydrogencarbonate solution and water
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffc3a281e5c14cc19f03b06d14717698
Source dataset
uspto-grants-1992_08
Patent number
US05138090

Reaction notes

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