Nitrogen → HCID 12566255, compound

HRID 42808Notes

Reaction equation

HRID 42808 reaction equation
N#N.[Br:3][C:4]1[CH:5]=[C:6]([C:9](=[O:11])[CH3:10])[S:7][CH:8]=1.COC([O:17][CH3:18])OC.[C:19]([O-])(O)=O.[Na+]>C(O)CO>[Br:3][C:4]1[CH:5]=[C:6]([C:9]2([CH3:10])[O:17][CH2:18][CH2:19][O:11]2)[S:7][CH:8]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 27352371-(4-Bromo-2-thienyl)ethan-1-one

Product 1

HCID 12566255HCID 12566255, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 1-(4-bromo-2-thienyl)ethan-1-one (2.00 g, 9.75 mmol) in ethylene glycol (10.7 mL) was treated with trimethylorthoformate (2.14 mL, 19.51 mmol) followed by LiBF4 (150 mg, 1.60 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. NaHCO3 (20 mL) was added and the mixture was extracted with EA (20 mL). The org. extracts were washed with brine (2×20 mL), dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:80 EA-Hept) gave the title compound as a white solid. TLC:rf (20:80 EA-Hept)=0.50. LC-MS-conditions 02: tR=0.99 min.

Workup

  1. extractionthe mixture was extracted with EA (20 mL)
  2. washextracts were washed with brine (2×20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (20:80 EA-Hept)

Sources & evidence

ORD record
ord-87f200fe70fe415fb6e632617a2c8cd5
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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