Hydrochloric Acid → 4-((Z)-(4-(2-fluorobenzyl)-3,4-dihydro-3-oxobenzo[b][1,4]thiazin-2-ylidene)methyl)benzoic acid

HRID 2407064Notes

Reaction equation

[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH2:9][S:8][C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]1=2.[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[CH:24][CH:23]=1)=O.CC[O-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])/[C:9](=[CH:20]/[C:22]2[CH:31]=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)/[S:8][C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]1=2

Participants

Conditions

Temperature: 70 °C

Procedure

4-(2-fluorobenzyl)-2H-benzo[b][1,4]thiazin-3(4H)-one (1 g, 3.66 mmole) and methyl 4-formylbenzoate (1.2 g) were dissolved in THF (20 mL) and to the solution was added NaOEt (1 g). The reaction solution was heated at 70 ° C. overnight and aqueous HCl (5%, 10 mL) was added to quench the reaction. The mixture was extracted with EtOAc (50 mL) twice and combined organic layers were dried over anhydrous magnisum sulfate. After filtration, the solvent was removed under vacuum to give 4-((Z)-(4-(2-fluorobenzyl)-3,4-dihydro-3-oxobenzo[b][1,4]thiazin-2-ylidene)methyl)benzoic acid (1.13 g, 71%).

Workup

customto quench
customthe reaction
extractionThe mixture was extracted with EtOAc (50 mL) twice
dry with materialwere dried over anhydrous magnisum sulfate
filtrationAfter filtration
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-aa0c0e4dcb1e4a88a98e1e0dcbc7f53f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809530B1

Reaction notes

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