Hydrochloric Acid → 5'-[3-(4-Chlorophenylsulfonyl)propyl]-2'-hydroxy-3-[2-(4-phenyl-2-thiazolyl)vinyl]benzanilide

HRID 1602487Notes

Reaction equation

HRID 1602487 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[N:12]=[C:13]([CH:16]=[CH:17][C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21]([OH:23])=O)[S:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[NH2:28][C:29]1[CH:34]=[C:33]([CH2:35][CH2:36][CH2:37][S:38]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)(=[O:40])=[O:39])[CH:32]=[CH:31][C:30]=1[OH:48].Cl>ClCCl.N1C=CC=CC=1>[Cl:47][C:44]1[CH:43]=[CH:42][C:41]([S:38]([CH2:37][CH2:36][CH2:35][C:33]2[CH:32]=[CH:31][C:30]([OH:48])=[C:29]([CH:34]=2)[NH:28][C:21](=[O:23])[C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([CH:17]=[CH:16][C:13]3[S:14][CH:15]=[C:11]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:12]=3)[CH:19]=2)(=[O:40])=[O:39])=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 196115102-Amino-4-[3-(4-chlorophenylsulfonyl)propyl]phenol hydrochlorideHCID 540264863-[2-(4-Phenyl-2-thiazolyl)vinyl]benzoic acid

Product 1

HCID 538477505'-[3-(4-Chlorophenylsulfonyl)propyl]-2'-hydroxy-3-[2-(4-phenyl-2-thiazolyl)vinyl]benzanilideYield 93%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (2 ml) was added to 3-[2-(4-phenyl-2-thiazolyl)vinyl]benzoic acid (0.45 g, 1.46 mmol), the mixture was stirred with heating under reflux for 30 minutes, and then the reaction solution was concentrated under reduced pressure. Toluene was added to the resulting residue, the mixture was concentrated under reduced pressure and, after repeating this step again, dried in vacuo. The resulting residue was added to a mixture of 2-amino-4-[3-(4-chlorophenylsulfonyl)propyl]phenol hydrochloride (0.50 g, 1.38 mmol), pyridine (3 ml) and dichloromethane (2 ml) with stirred under ice-cooling, followed by 12 hours of reaction at room temperature. The reaction solution was poured into ice and 1 N hydrochloric acid and the solid precipitated was collected by filtration. By washing the collected solid with ethanol, 5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-hydroxy-3-[2-(4-phenyl-2-thiazolyl)vinyl]benzanilide (0.79 g, 1.28 mmol, 93%) was obtained as a solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 30 minutes
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. additionToluene was added to the resulting residue
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customdried in vacuo
  7. stirringwith stirred under ice-
  8. temperaturecooling
  9. customfollowed by 12 hours of reaction at room temperature
  10. customthe solid precipitated
  11. filtrationwas collected by filtration
  12. washBy washing the collected solid with ethanol

Sources & evidence

ORD record
ord-6e7e81e96fde454a92f45e0e7212e931
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

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