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

HRID 2096101Notes

Reaction equation

HRID 2096101 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+].CN(C)C=O.Cl>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 6228DimethylformamideHCID 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 962WaterSolvent

Procedure

The obtained 4-methoxy-4′-(di-p-tolylamino)stilbene and two equivalent amounts of sodium ethanethiolate were dissolved into N,N-dimethylformamide, allowing reaction to proceed at 130° C. for 5 hours. The solution was cooled, added in water, and neutralized with hydrochloric acid, and the target product was extracted with ethyl acetate. The extract liquid was washed with water and dried, and solvent was removed to obtain a crude product, which was then purified by column chromatography on silica gel to give 4-hydroxy-4′-(di-p-tolylamino)stilbene (CTP-1), a target product.

Workup

  1. customreaction
  2. temperatureThe solution was cooled
  3. extractionthe target product was extracted with ethyl acetate
  4. washThe extract liquid was washed with water
  5. customdried
  6. customsolvent was removed
  7. customto obtain a crude product, which
  8. customwas then purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8d5304243bcd4ebb8a615f1ac18b9557
Source dataset
uspto-grants-2013_05
Patent number
US08450033B2

Reaction notes

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