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

HRID 1637236Notes

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

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. 1H NMR (CDCl3) δ12.47 (s, 1 H), 7.29 (s, 1 H), 6.61 (s, 1 H), 3.91 (s, 2 H), 2.64 (q, J=7.6 Hz, 2 H), 2.25 (s, 3 H), 1.21 (t, J=7.6 Hz, 3 H) ppm; MS m/e 284 (M+H)+ ;

Workup

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

Sources & evidence

ORD record: ord-78028382d36e4f7594de23b8dfd9728c
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06040321

Reaction notes

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