Thionyl Chloride → N1-(S-(4-methoxybenzyl) thiosalicyloyl)-N4-methylpiperazine

HRID 1263476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1263476
C(SC1C(=CC=CC=1)C(Cl)=O)C1C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:36]=[CH:35][C:23]([CH2:24][S:25][C:26]2[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28]([OH:30])=O)=[CH:22][CH:21]=1.O=S(Cl)Cl.[CH3:41][N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>C1C=CC=CC=1.O>[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][S:25][C:26]2[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28]([N:45]2[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]2)=[O:30])=[CH:35][CH:36]=1

Komponenten

7

Edukt 4

HCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 3568003Benzoic acid, 2-[[(4-methoxyphenyl)methyl]thio]-HCID 200673402-[(Phenylmethyl)thio]benzoyl chloride

Produkt 1

HCID 69733570N1-(S-(4-methoxybenzyl) thiosalicyloyl)-N4-methylpiperazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

The compound N1-(S-(4-methoxybenzyl) thiosalicyloyl)-N4-methylpiperazine (compound 2) was prepared in a manner similar to that described above for S-(4-methoxybenzyl)-N-(2-(N′,N′-dimethylamino)ethyl) thiosalicylamide. After preparing the S-benzylthiosalicyloyl chloride from 0.02M(5.487 g) of S-(4-methoxybenzyl)thiosalicylic acid and 20 mL of SOCl2, the mixture was suspended in warm benzene (30 mL) and was slowly added to a 20 mL cold solution of 4.007 g(0.04M) 1-methylpiperazine in benzene. The mixture was stirred overnight at room temperature. The next day 40 mL of water were added, the aqueous layer was separated, and extracted twice with 15 mL CH2Cl2. The extracts were combined with the benzene layer, washed with 10% NaOH solution and dried over anhydrous MgSO4. Removal of the solvents under reduced pressure left an oily product which was dissolved in petroleum ether (10 ml). A precipitate separated out upon cooling in an ice bath. The separated solid was collected by suction filtration and washed with petroleum ether to give 3.372 g(47%) of the product in the form of white crystals and having a melting point of 77-78° C. and the following specifications:

Aufarbeitung

  1. customthe aqueous layer was separated
  2. extractionextracted twice with 15 mL CH2Cl2
  3. washwashed with 10% NaOH solution
  4. dry with materialdried over anhydrous MgSO4
  5. customRemoval of the solvents under reduced pressure
  6. waitleft an oily product which
  7. dissolutionwas dissolved in petroleum ether (10 ml)
  8. customA precipitate separated out
  9. temperatureupon cooling in an ice bath
  10. filtrationThe separated solid was collected by suction filtration
  11. washwashed with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-3834619c89ec4b82ae456e520aef33d7
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541479B1

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