Hydrochloric Acid → 4-(2-{4-[Bis(4-methylphenyl)amino]phenyl}ethenyl)phenol

HRID 597757Notes

Reaction equation

HRID 597757 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C([S-])C.[Na+].O.Cl>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4459711Sodium ethanethiolateHCID 538532054-[2-(4-Methoxyphenyl)ethenyl]-N,N-bis(4-methylphenyl)aniline

Product 1

HCID 599226714-(2-{4-[Bis(4-methylphenyl)amino]phenyl}ethenyl)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The above-prepared 4-methoxy-4′-(di-p-tolylamino)stilbene and twice equimolar amount of sodium ethanethiolate are dissolved in N,N-dimethylformamide, and reacted for 5 hours at 130° C. The mixture is cooled down, and then poured into water and neutralized with hydrochloric acid. The objective material is extracted therefrom using acetic acid. The extracted liquid is washed with water, and then dried. The crude objective material is prepared by removing the solvent (i.e., N,N-dimethylformamide) therefrom. Further, the crude objective material is purified with a column chromatography using silica gel. Thus, 4-hydroxy-4′-(di-p-tolylamino)stilbene (i.e., objective material) is prepared.

Workup

  1. customreacted for 5 hours at 130° C
  2. temperatureThe mixture is cooled down
  3. extractionThe objective material is extracted
  4. washThe extracted liquid is washed with water
  5. customdried
  6. customThe crude objective material is prepared
  7. customby removing the solvent (i.e., N,N-dimethylformamide)
  8. customFurther, the crude objective material is purified with a column chromatography

Sources & evidence

ORD record
ord-e17cb4e29a2045389be54ddeb6b732f3
Source dataset
uspto-grants-2011_03
Patent number
US07897313B2

Reaction notes

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