2,6-Dimethylaniline → HCID 20512402, compound

HRID 1164439Notes

Reaction equation

HRID 1164439 reaction equation
Br[CH:2]([CH3:13])[CH2:3][NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12].[CH3:14][C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:16]=1[NH2:17]>[I-].[K+].Cl>[CH3:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=1[NH:4][CH2:3][CH:2]([NH:17][C:16]1[C:18]([CH3:22])=[CH:19][CH:20]=[CH:21][C:15]=1[CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 68962,6-DimethylanilineHCID 20512395HCID 20512395, compound

Product 1

HCID 20512402HCID 20512402, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 313Hydrochloric AcidSolvent2×

Procedure

A mixture of 106.8 g (0.441 moles) of N-(β-bromopropyl)-2,6-dimethyl-aniline, obtained as described in point (a) above, 110 ml (107.4 g, 0.88 moles) of 2,6-dimethyl-aniline and 1.6 g (10 mmoles) of potassium iodide is stirred at 100° to 105° C. for 3 hours under nitrogen atmosphere. The mixture is allowed to cool, 600 ml of 10% aqueous hydrochloric acid are added, and the resulting mixture is allowed to stand at room temperature overnight. The separated precipitate, which is a mixture of the hydrochloride and the hydrobromide of the expected product, is filtered off, washed with water, dried, and then treated as described in point (b) of Method (b) above in order to liberate the base. In this way 93.8 g (75.3%) of 1,2-bis(2',6'-dimethylphenyl-amino)-propane are obtained; m.p.: 54°-56° C.

Workup

  1. customobtained
  2. temperatureto cool
  3. waitto stand at room temperature overnight
  4. filtrationthe hydrobromide of the expected product, is filtered off
  5. washwashed with water
  6. customdried
  7. additiontreated

Sources & evidence

ORD record
ord-70b40d798d064bf1aa79bb372c1b2359
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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