Acetic Acid → N-{4-[2-(4-formylthiophen-2-yl)vinyl]-1,3-thiazol-2-yl}acetamide

HRID 1892512Notes

Reaction equation

[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)[S:9][CH:10]=1.C(O)(=O)C.O1CCCC1>O>[CH:2]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)[S:9][CH:10]=1)=[O:1]

Participants

Conditions

Temperature: 55 °C

Procedure

To N-(4-{2-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]vinyl}-1,3-thiazol-2-yl)acetamide (1.418 g, 4.398 mmol) were added acetic acid (16.8 ml), tetrahydrofuran (5.6 ml) and water (5.6 ml), and the mixture was stirred at 55° C. for 2.5 hr. The reaction mixture was concentrated, and diisopropyl ether was added. The precipitated solid was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give N-{4-[2-(4-formylthiophen-2-yl)vinyl]-1,3-thiazol-2-yl}acetamide (1.136 g, 4.081 mmol, yield 92.8%) as a pale-yellow solid.

Workup

concentrationThe reaction mixture was concentrated
additiondiisopropyl ether was added
filtrationThe precipitated solid was collected by filtration
washwashed with diisopropyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-07cd235ca0464e05a0689adc1ff5bffd
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507690B2

Reaction notes

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