Furan → 2-(2-furyl)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one

HRID 2292040Notes

Reaction equation

ClC1C=C(C=CC=1)C(O[CH:8]1[C:13](=[O:14])[NH:12][C:11]([CH3:15])=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[S:9]1)=O.[O:25]1[CH:29]=[CH:28][CH:27]=[CH:26]1>C(#N)C>[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH:8]1[C:13](=[O:14])[NH:12][C:11]([CH3:15])=[C:10]([C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)[S:9]1

Participants

Conditions

Temperature: 50 °C

Procedure

Silica gel (Wakogel C-200, 0.03 g) was added as catalyst to a solution of 2-(3-chlorobenzoyloxy)-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (0.79 g) and furan (0.30 g) in acetonitrile (30 ml) and the mixture was stirred at 50° C. for 35 hours. The mixture was chromatographed on silica gel (Wakogel C-200) column, using acetonitrile as an eluant. The residue was recrystallized from acetonitrile to give the titled compound (0.23 g, yield 37.7%) as pale orange crystals.

Workup

customThe mixture was chromatographed on silica gel (Wakogel C-200) column
customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record: ord-86f187cdb12d4511b7c283780dbbf6eb
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04800201

Reaction notes

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