Nitrogen → 2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-thioacetamide

HRID 1189427Notes

Reaction equation

HRID 1189427 reaction equation
N#N.C[Si](C)(C)[S:5][Si](C)(C)C.C[O-].[Na+].[CH3:15][C:16]1([C:21]2[O:25][C:24]([CH2:26][C:27]#[N:28])=[CH:23][CH:22]=2)[O:20][CH2:19][CH2:18][O:17]1>CN(C=O)C.O>[CH3:15][C:16]1([C:21]2[O:25][C:24]([CH2:26][C:27]([NH2:28])=[S:5])=[CH:23][CH:22]=2)[O:17][CH2:18][CH2:19][O:20]1

Participants

7

Reactant 4

HCID 947NitrogenHCID 76920Disilathiane, 1,1,1,3,3,3-hexamethyl-HCID 10942334Sodium MethoxideHCID 67128458[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-acetonitrile

Product 1

HCID 866649202-[5-(2-Methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-thioacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), hexamethyldisilthiane (9.45 mL, 45.07 mmol) was added dropwise to a solution of NaOMe (2.51 g, 45.07 mmol) in dry DMF (40 mL) and the reaction mixture was stirred at rt for 15 min. This dark blue solution was then added to a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-acetonitrile (3.48 g, 18.03 mmol) in DMF (30 mL) and the reaction mixture was stirred for 16 h at rt. Water (300 mL) was then added and the mixture was extracted twice with EA (300 mL). The combined org. phases were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (6:4 hept-EA) gave the title compound as a yellow oil. TLC: rf (6:4 hept-EA)=0.18. LC-MS-conditions 02: tR=0.74 min, [M+H]+=228.44.

Workup

  1. stirringthe reaction mixture was stirred for 16 h at rt
  2. extractionthe mixture was extracted twice with EA (300 mL)
  3. dry with materialphases were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (6:4 hept-EA)

Sources & evidence

ORD record
ord-1ba0fd3315d846eaa2195df73a910dad
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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