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Acetic Acid → 3-Amino-N,N-dimethyl-4-[2-(3-thienyl)-1H-imidazol-1-yl]-benzamide

HRID 72754
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 72754
[CH3:1][N:2]([CH3:24])[C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)=[C:6]([N+:20]([O-])=O)[CH:5]=1.C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+].N>O1CCCC1.C(OCC)(=O)C.O>[NH2:20][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15]1[CH:19]=[CH:18][S:17][CH:16]=1)[C:3]([N:2]([CH3:24])[CH3:1])=[O:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 24477Sodium ThiosulfateHCID 59198669N,N-dimethyl-3-nitro-4-[2-(3-thienyl)-1H-imidazol-1-yl]benzamide

Produkt 1

HCID 591988023-Amino-N,N-dimethyl-4-[2-(3-thienyl)-1H-imidazol-1-yl]-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 1.60 g of N,N-dimethyl-3-nitro-4-[2-(3-thienyl)-1H-imidazol-1-yl]benzamide, 5.8 mL of acetic acid and 5.8 mL of water were added, and dissolved under heating. To the solution 3.25 g of 85% sodium hyposulfite was added little by little, followed by 3.3 hours' heating under reflux. The reaction liquid was cooled with ice, to which ethyl acetate was added, and then 25% aqueous ammonia was added little by little to render the same weakly alkaline. Tetrahydrofuran was added and whereby separated organic layer was recovered, which was washed with brine and dried over magnesium sulfate. Distilling the solvent off, 769 mg of the title compound was obtained.

Aufarbeitung

  1. dissolutiondissolved
  2. temperatureunder heating
  3. temperature' heating
  4. temperatureunder reflux
  5. customThe reaction liquid
  6. additionwas added
  7. customwhereby separated organic layer
  8. customwas recovered
  9. washwhich was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. distillationDistilling the solvent off, 769 mg of the title compound
  12. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-bd127e06abcd416f8ca97540e6fe1708
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829000B2

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