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Hydrochloric Acid → (E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride

HRID 48330
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 48330
[ClH:1].Cl.[CH2:3]([S:10][C:11]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][C:12]=1[CH:13]=[CH:14][C:15]1=[N:16][CH2:17][CH2:18][N:19]([CH3:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]1=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Sn](Cl)[Cl:35].Cl>O1CCCC1.C(O)C>[ClH:35].[ClH:1].[CH2:3]([S:10][C:11]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][C:12]=1/[CH:13]=[CH:14]/[C:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]([CH3:26])[CH2:18][CH2:17][N:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 69893360(E)-5-(2-benzylthio-5-nitrostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepine dihydrochloride

Produkt 1

HCID 22742398(E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochlorideAusbeute 19,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 215 mg (0.50 mmol) of (E)-5-(2-benzylthio-5-nitrostyryl)-2,3-dihydro-1-methyl-1H-1,4-benzodiazepine dihydrochloride (prepared as described in Example 15) in 8 ml of tetrahydrofuran and 8 ml of ethanol was added 380 mg (0.90 mmol) of tin (II) chloride and 0.48 ml of concentrated hydrochloric acid. The mixture was heated at 60° C. for 7 hours. The solution was reduced to half volume and partitioned between 50 ml of saturated sodium hydrogen carbonate solution and 100 ml and 50 ml of dichloromethane. The combined organic phases were dried (magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography eluting with 2-5% methanol/dichloromethane and treated with 0.30 ml of 4M hydrogen chloride in dioxan. The solvent was evaporated and the residue was recrystallised from methanol/ether to give 46 mg of (E)-4-benzylthio-3-[2-(2,3-dihydro-1-methyl-1H-1,4-benzodiazepin-5-yl)vinyl]aniline dihydrochloride as dark red crystals; MS: m/e 400 [M+H]+.

Aufarbeitung

  1. custompartitioned between 50 ml of saturated sodium hydrogen carbonate solution and 100 ml and 50 ml of dichloromethane
  2. dry with materialThe combined organic phases were dried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with 2-5% methanol/dichloromethane
  7. additiontreated with 0.30 ml of 4M hydrogen chloride in dioxan
  8. customThe solvent was evaporated
  9. customthe residue was recrystallised from methanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-e3db9b8b46ee4afa84e47cc28b26c4e1
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06703387B2

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