2-[3-sulfanyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-4-yl]acetic acid → 4-(2-Hydroxy-ethyl)-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione

HRID 732033

Reaktionsgleichung

Reaktionsgleichung von HRID 732033
[H-].[H-].[H-].[H-].[Li+].[Al+3].[S:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]1[N:16]([CH2:17][C:18](O)=[O:19])[C:15](=[S:21])[NH:14][N:13]=1>C1COCC1>[OH:19][CH2:18][CH2:17][N:16]1[C:12]([C:8]2[S:7][CH:11]=[CH:10][CH:9]=2)=[N:13][NH:14][C:15]1=[S:21]

Komponenten

4

Edukt 2

HCID 49625532-[3-sulfanyl-5-(thiophen-2-yl)-4H-1,2,4-triazol-4-yl]acetic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 859371364-(2-Hydroxy-ethyl)-5-thiophen-2-yl-2,4-dihydro-[1,2,4]triazole-3-thione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a slurry of LAH (38.1 mg, 1.00 mmol) in anhydrous THF (8 ml) was drop wise added (3-thiophen-2-yl-5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-acetic acid (101 mg, 0.42 mmol) in anhydrous THF (4 ml). The mixture was reacted for 2 h and then quenched with saturated aq. Na2SO4 (10 ml). THF was removed under reduced pressure and the residue was made acidic with aq. HCl (3N) and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine (15 ml), dried (MgSO4) and concentrated under reduced pressure. The crude product was used without purification in the next step. 1H NMR (DMSO-d6), δ (ppm): 13.94 (s, 1H), 7.86 (d, 1H); 7.81 (d, 1H), 7.24 (dd, 1H), 5.09 (t, 1H), 4.16 (t, 2H), 3.76 (app. q, 2H).

Aufarbeitung

  1. customThe mixture was reacted for 2 h
  2. customquenched with saturated aq. Na2SO4 (10 ml)
  3. customTHF was removed under reduced pressure
  4. custompartitioned between EtOAc and water
  5. extractionThe aqueous layer was extracted with EtOAc (3×20 ml)
  6. washThe combined organic layers were washed with brine (15 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was used without purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-3004171146ff4bd4bf403b0ec1f452cd
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585881B2

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