Formamide → Methyl 4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

HRID 1051954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051954
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]([NH2:17])=O.Br[CH:19]1[C:24](=O)[CH2:23][CH2:22][CH2:21][CH:20]1[C:26]([O:28][CH3:29])=[O:27]>O1CCOCC1>[S:2]1[C:19]2[CH:20]([C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:22][CH2:23][C:24]=2[N:17]=[CH:15]1

Komponenten

5

Edukt 3

HCID 713FormamideHCID 14817Phosphorus sulfide (P2S5)HCID 83646766HCID 83646766, Verbindung

Produkt 1

HCID 90303216Methyl 4,5,6,7-tetrahydrobenzo[d]thiazole-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

At 0° C., finely crushed P4S10 (9.35 g, 21.0 mmol) was added to a mixture of formamide (4.73 g, 105.0 mmol) in dioxane (28.5 mL). Subsequently, the mixture was stirred in a sealed vial at 100° C. for 1.5 h, cooled to RT and filtrated. The filtrate was added to a mixture of methyl 2-bromo-3-oxocyclohexanecarboxylate (2.06 g, 8.76 mmol) in dioxane (16.5 mL) and stirred in a sealed vial at 80° C. overnight. The mixture was quenched by the addition of aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. Purification by means of CC (10-40% EtOAc/Hept) provided a yellow oil.

Aufarbeitung

  1. temperaturecooled to RT
  2. filtrationfiltrated
  3. stirringstirred in a sealed vial at 80° C. overnight
  4. customThe mixture was quenched by the addition of aq. sat. NaHCO3
  5. extractionextracted with EtOAc
  6. washlayers were washed with brine
  7. dry with materialdried over MgSO4
  8. customPurification by means of CC (10-40% EtOAc/Hept)
  9. customprovided a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-263acd6711eb446e9db5559b644bf796
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388198B2

Notizen zur Reaktion

Wird geladen…