Sulfuric Acid → N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide

HRID 1060243Notes

Reaction equation

HRID 1060243 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([S:10][CH2:11][C:12]([NH:14][CH2:15][C:16](=[O:19])[CH2:17][CH3:18])=O)=[CH:8][N:9]=1)(=[O:3])[CH3:2].S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[CH2:17]([C:16]1[O:19][C:12]([CH2:11][S:10][C:7]2[S:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[N:9][CH:8]=2)=[N:14][CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 10946551[[2-(acetylamino)-5-thiazolyl]thio]-N-(2-oxobutyl)acetamide

Product 1

HCID 5329663N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamideYield 43%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of [[2-(acetylamino)-5-thiazolyl]thio]-N-(2-oxobutyl)acetamide (10.5 g, 34.8 mmol) in acetic anhydride (100 mL) was added conc. sulfuric acid (10 mL). The mixture was stirred at 55-60° C. for 2 h and sodium acetate (15 g, 0.18 mol) was added to the mixture. The mixture was concentrated in vacuo. To the residue was added cold water (100 mL). The precipitated solid was collected, washed with water and dried. It was purified by a flash column chromatography (SiO2; methylene chloride: MeOH/100:5) to afford N-[5-[[(5-ethyl-2-oxazolyl)methyl]thio]-2-thiazolyl]acetamide (4.2 g, 43%) as a solid, mp 147-148° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added cold water (100 mL)
  3. customThe precipitated solid was collected
  4. washwashed with water
  5. customdried
  6. customIt was purified by a flash column chromatography (SiO2; methylene chloride: MeOH/100:5)

Sources & evidence

ORD record
ord-17e90c8e4a1245dfbbad516ac867617a
Source dataset
uspto-grants-2003_02
Patent number
US06521759B2

Reaction notes

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