Water → alpha-(2-Benzothiazolylthio)(m-phenoxyphenyl)acetonitrile

HRID 1759442

Reaktionsgleichung

Reaktionsgleichung von HRID 1759442
C1(C)C=CC(S(O[CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:15]=2)[C:12]#[N:13])(=O)=O)=CC=1.[Na].[SH:29][C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1.O>COCCOC>[S:31]1[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=[C:30]1[S:29][CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:15]=1)[C:12]#[N:13]

Komponenten

6

Edukt 4

HCID 962WaterHCID 5360545SodiumHCID 12945136O-(p-toluenesulfonyl)-m-phenoxymandelonitrileHCID 178418395HCID 178418395, Verbindung

Produkt 1

HCID 20532030alpha-(2-Benzothiazolylthio)(m-phenoxyphenyl)acetonitrileAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

1.517 g of O-[p-toluenesulfonyl)-m-phenoxymandelonitrile was dissolved in 5 ml of DME, and the solution was stirred in an argon atmosphere under ice cooling. Sodium salt of 2-mercaptobenzothiazole (760 mg) was added, and the mixture was stirred under ice cooling for 30 minutes, and then at room temperature for 1.5 hours. Water (20 ml) was added to the reaction mixture, and it was extracted with 20 ml of methylene chloride three times. The extract was washed with 10 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; benzene and methylene chloride) to afford 1.233 g (yield 85%) of alpha-(2-benzothiazolylthio)(m-phenoxyphenyl)acetonitrile as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred under ice cooling for 30 minutes
  2. extractionwas extracted with 20 ml of methylene chloride three times
  3. washThe extract was washed with 10 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel; benzene and methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-9978d8620b444b699ef6db7c7ebd0a78
Quelldatensatz
uspto-grants-1982_07
Patentnummer
US04340740

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