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

HRID 2407064
Notes
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Reaction equation

HRID 2407064 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15294Methyl 4-FormylbenzoateHCID 2723922Sodium ethoxideHCID 32444154-(2-fluorobenzyl)-2H-benzo[b][1,4]thiazin-3(4H)-one

Product 1

HCID 585388614-((Z)-(4-(2-fluorobenzyl)-3,4-dihydro-3-oxobenzo[b][1,4]thiazin-2-ylidene)methyl)benzoic acidYield 76.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with EtOAc (50 mL) twice
  4. dry with materialwere dried over anhydrous magnisum sulfate
  5. filtrationAfter filtration
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes