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Hydrochloric Acid → HCID 20350647, Verbindung

HRID 1449236
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1449236
[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]=[C:24]([S:27](C)=O)SC)[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(Cl)Cl.[OH2:34].[CH3:35][O:36][CH2:37][CH2:38][O:39]C>>[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:37][C:38]([OH:39])=[O:34])[C:9]1[C:10]([Cl:16])=[CH:11][CH:12]=[CH:13][C:14]=1[Cl:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([N:8]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([O:36][CH3:35])=[S:27])[C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 6344DichloromethaneHCID 80711,2-DimethoxyethaneHCID 54175266HCID 54175266, Verbindung

Produkt 2

HCID 13023173HCID 13023173, VerbindungAusbeute 14 %
HCID 20350647
HCID 20350647, Verbindung
Ausbeute 81 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In 26 ml of 1,2-dimethoxyethane, 1.2 g (0.0026 mole) of 1-[N-benzyl-o-(2,6-dichloroanilino)phenyl]-2-methylsulfinyl-2-methylthioethylene was dissolved and then, 13 ml of conc. HCl was added and the mixture was stirred at 80° C. for 4 hours. The reaction mixture was cooled and 80 ml of methylene chloride and 10 ml of water were added to extract the reaction product and the separated water phase was further mixed with 70 ml of methylene chloride to extract the reaction product. Both of methylene chloride phases were combined, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was separated by a column chromatography (silica gel: Wako gel Q-23 manufactured by Wako Junyaku and developing solvent:n-hexane:acetone=2:1) to obtain 0.14 g (yield: 14%) of N-benzyl-o-(2,6-dichloroanilino)phenyl acetic acid and 0.88 g (yield: 81%) of methyl N-benzyl-o-(2,6-dichloroanilino)phenylthioacetate.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionto extract the reaction product
  3. additionthe separated water phase was further mixed with 70 ml of methylene chloride
  4. extractionto extract the reaction product
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by a column chromatography (silica gel: Wako gel Q-23 manufactured by Wako Junyaku and developing solvent:n-hexane:acetone=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ddffbd3595b24f63825b6be4d2dae32e
Quelldatensatz
uspto-grants-1980_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04189595

Notizen zur Reaktion

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