Sodium Hydroxide → HCID 67297682, compound

HRID 925031Notes

Reaction equation

HRID 925031 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27])([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[N:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:21]([CH3:24])([CH3:23])[CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 805742-tert-ButylanilineHCID 893019HCID 893019, compound

Product 1

HCID 67297682HCID 67297682, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-tert-butyl-N-(chloro(p-tolyl)methylene)benzenamine (HS Imine II) (2.86 g, 10 mmol) was dissolved in 50 mL of toluene. 2-tert-butylaniline (1.56 mL, 10 mmol) was added dropwise at room temperature, resulting in a yellow solution, which was refluxed overnight. Toluene was removed under vacuum. Sodium hydroxide (100 mL of 0.10 M solution, 10 mmol) was added and the solution was stirred for 1 hour. The solid that deposited was extracted into 150 mL of diethylether. The ether layer was dried with MgSO4, filtered, and taken to dryness, leaving 3.72 g (93%) of white solid. The 1H NMR spectrum is complex and is consistent with a mixture of E/Z isomers.

Workup

  1. customresulting in a yellow solution, which
  2. temperaturewas refluxed overnight
  3. customToluene was removed under vacuum
  4. extractionThe solid that deposited was extracted into 150 mL of diethylether
  5. dry with materialThe ether layer was dried with MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-bf55c57a19924afe8384ddf4571fb47d
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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