Sodium Bicarbonate → N-[5-[[(4,5-dimethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide

HRID 1385192Notes

Reaction equation

HRID 1385192 reaction equation
[C:1]([S:4][C:5]1[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][CH:6]=1)(=O)[CH3:2].CC(C)([O-])C.[K+].BrCC1[O:23][C:24]([CH3:28])=[C:25]([CH3:27])[N:26]=1.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:27][C:25]1[N:26]=[C:2]([CH2:1][S:4][C:5]2[S:9][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[N:7][CH:6]=2)[O:23][C:24]=1[CH3:28]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 118302042-(Bromomethyl)-4,5-dimethyl-1,3-oxazoleHCID 22481077S-(2-(Acetylamino)-5-thiazolyl) ethanethioateHCID 23665647Potassium tert-butoxide

Product 1

HCID 5329684N-[5-[[(4,5-dimethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamideYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[5-(Acetylthio)-2-thiazolyl]acetamide (0.050 g, 0.23 mmol) was dissolved in dry THF (10 ml) and here potassiumtert-butoxide (1.0 M solution in THF, 0.25 ml, 0.25 mmol) was added to the mixture. The reaction mixture was stirred at rt for 15 min., and 2-(bromomethyl)-4,5-dimethyloxazole (0.064 g, 0.34 mmol) was added to this mixture. The reaction mixture was stirred at rt for 3 h and saturated aqueous NaHCO3 solution (20 mL) was added to the mixture. The organic layer was separated and the aqueous layer was extracted with dichloromethane (1×20 mL). The combined organic layers was concentrated. The residue was purified by flash column chromatography (SiO2; methanol:dichloromethane/1:20) to afford N-[5-[[(4,5-dimethyl-2-oxazolyl)methyl]thio]-2-thiazolyl] acetamide (15 mg, 23%) as a yellow solid. 1H NMR (CDCl3) δ 11.78 (s, 1H), 7.38 (s, 1H), 3.90 (s, 2H), 2.30 (s, 3H), 2.22 (s 3H), 2.05 (s, 3H); MS m/e 284 (M+H)+;

Workup

  1. stirringThe reaction mixture was stirred at rt for 3 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (1×20 mL)
  4. concentrationThe combined organic layers was concentrated
  5. customThe residue was purified by flash column chromatography (SiO2; methanol:dichloromethane/1:20)

Sources & evidence

ORD record
ord-69b19a21646f40dc9fe54455d2bb341b
Source dataset
uspto-grants-2001_07
Patent number
US06262096B1

Reaction notes

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