Sodium Hydroxide → Dibenzyl-(4-iodo-2,5-dimethylphenyl)amine

HRID 1094952Notes

Reaction equation

HRID 1094952 reaction equation
Cl.[CH2:2]([N:9]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([I:17])=[CH:12][C:11]=1[CH3:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:19]([N:9]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([I:17])=[CH:12][C:11]=1[CH3:18])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57461071HCID 57461071, compound

Product 1

HCID 57461072Dibenzyl-(4-iodo-2,5-dimethylphenyl)amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The dibenzyl-(4-iodo-2,5-dimethylphenyl)amine hydrochloride was transferred to a 3 L flask and toluene (1 L) and 1 M aqueous sodium hydroxide (1 L) were added. The resulting mixture was stirred for 1 hour and then the layers were separated. The organic layer was washed with dilute brine (500 mL) and the solvent was removed by rotoevaporation to provide dibenzyl-(4-iodo-2,5-dimethylphenyl)amine (80 g) as a semi-solid thick oil. (Alternatively, dichloromethane can be used in place of toluene in this step). 1H NMR (300 MHz, DMSO-d6) δ 2.05 (s, 3H), 2.19 (s, 3H), 3.90 (s, 4H), 6.91 (s, 1H), 7.05-7.20 (m, 10H), 7.42 (s, 1H); MS [M+H+] found 428.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with dilute brine (500 mL)
  3. customthe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-d76c64de6ec64651bb46494ff1b4e184
Source dataset
uspto-grants-2012_03
Patent number
US08134006B2

Reaction notes

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