Nitrogen → 2-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

HRID 1044753

Reaction equation

HRID 1044753 reaction equation
N#N.[Br:3][C:4]1[S:5][C:6]([C:9](=[O:11])[CH3:10])=[CH:7][N:8]=1.COC([O:17][CH3:18])OC.[C:19]([O-])(O)=O.[Na+]>C(O)CO>[Br:3][C:4]1[S:5][C:6]([C:9]2([CH3:10])[O:17][CH2:18][CH2:19][O:11]2)=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 575628131-(2-Bromo-1,3-thiazol-5-yl)ethan-1-one

Product 1

HCID 668200782-Bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-thiazole

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 a condenser under inert atmosphere (N2), a solution of 1-(2-bromo-thiazol-5-yl)-ethanone (16.22 g, 78.71 mmol) in ethylene glycol (85 mL) was treated with trimethylorthoformate (18 mL, 164.19 mmol) followed by LiBF4 (1.51 g, 15.74 mmol). The reaction mixture was heated at 95° C. for 2 days. Sat. aq. NaHCO3 was added and the mixture was extracted with Et2O (3×). The org. extracts were washed with brine, dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 3:1 hept-EA) gave the title compound as a yellow solid. TLC:rf (1:1 hept-EA)=0.63. LC-MS-conditions 02: tR=0.89 min; [M+H]+=250.24.

Workup

  1. extractionthe mixture was extracted with Et2O (3×)
  2. washextracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (20:1 to 3:1 hept-EA)

Sources & evidence

ORD record
ord-310be4375919419b9130be1b8e51e298
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Linked notes

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