Sodium borohydride → N-[(2-chloro-5-thiazolyl)methyl]-3-phenyl-2-pyridinamine

HRID 1023276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023276
[Cl:1][C:2]1[S:3][C:4]([CH:7]=[N:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][N:6]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][N:6]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 66973405N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine2×

Produkt 1

HCID 66973263N-[(2-chloro-5-thiazolyl)methyl]-3-phenyl-2-pyridinamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N-[(2-chloro-5-thiazolyl)methylene]-3-phenyl-2-pyridinamine (i.e. the product of Step B) was added portionwise to a stiffed excess of sodium borohydride (0.379 g, 100 mmol) in methanol (8 mL). After addition was complete, the reaction mixture was allowed to stir for 5 min at ambient temperature. The excess reducing agent was quenched by adding glacial acetic acid until gas evolution ceased. Water (20 mL) was added, and the reaction mixture was concentrated to remove methanol. The resulting aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried (MgSO4) and concentrated to give the title compound as a yellow solid (0.659 g).

Aufarbeitung

  1. additionAfter addition
  2. customwas quenched
  3. additionby adding glacial acetic acid until gas evolution
  4. additionWater (20 mL) was added
  5. concentrationthe reaction mixture was concentrated
  6. customto remove methanol
  7. extractionThe resulting aqueous phase was extracted twice with ethyl acetate
  8. dry with materialthe combined organic phases were dried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ed2c9ea131f470eac269f99053b91d8
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722690B2

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