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Ammonia → 4-Chloro-2-(3-aminomethyl-2-methysulfanyl-phenoxy)-benzonitrile fumarate

HRID 1243760
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1243760
[NH3:1].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18]Cl)[C:13]=2[S:20][CH3:21])[CH:4]=1.[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26]>CO>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][NH2:1])[C:13]=2[S:20][CH3:21])[CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 444972Fumaric AcidHCID 219304424-Chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile2×

Produkt 1

HCID 694233764-Chloro-2-(3-aminomethyl-2-methysulfanyl-phenoxy)-benzonitrile fumarate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

7N Ammonia in methanol (30 mL, 210 mmol) was added to 4-chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile (240 mg, 0.8 mmol). After stirring for 17 h, TLC still showed some 4-chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile. The reaction mixture was concentrated to about 10 mL by evaporation in vacuo, concentrated ammonia (7 mL) was added and the mixture was heated with stirring at 60° C. for 17 h. Sodium carbonate solution (4 mL) and ethyl acetate (6 mL) were added and the organic layer was separated and dried with MgSO4. To this, was added fumaric acid (84 mg, 0.64 mmol) in methanol (3 mL). Immediately, the solvent was removed in vacuo and diethyl ether (40 mL) was added to the residue. After stirring for 17 h, 4-chloro-2-(3-aminomethyl-2-methysulfanyl-phenoxy)-benzonitrile fumarate (134.7 mg, 53%) was filtered off as a white solid.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to about 10 mL by evaporation in vacuo, concentrated ammonia (7 mL)
  2. additionwas added
  3. temperaturethe mixture was heated
  4. stirringwith stirring at 60° C. for 17 h
  5. additionSodium carbonate solution (4 mL) and ethyl acetate (6 mL) were added
  6. customthe organic layer was separated
  7. dry with materialdried with MgSO4
  8. customImmediately, the solvent was removed in vacuo and diethyl ether (40 mL)
  9. additionwas added to the residue
  10. stirringAfter stirring for 17 h
  11. filtration4-chloro-2-(3-aminomethyl-2-methysulfanyl-phenoxy)-benzonitrile fumarate (134.7 mg, 53%) was filtered off as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-266b3bc613b04a158bd8b746845f5821
Quelldatensatz
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07119122B2

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