5-Nitrofurfural → HCID 178423499, compound

HRID 1696625Notes

Reaction equation

[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[N+]([C:17]1[O:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=1)([O-])=O>O1CCCC1.O.C(OCC)(=O)C>[CH3:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([S:1][C:17]3[O:21][C:20]([CH:22]=[O:23])=[CH:19][CH:18]=3)=[N:3][C:4]=2[CH:10]=1

Participants

Conditions

Temperature: 20 °C

Procedure

1.16 g of 2-mercapto-5-methylbenzimidazole in 14 mL of tetrahydrofurane (THF) are dropped into a 100 mL three-neck flask, and then 309 mg of sodium hydride is added. The mixture is stirred at reflux temperature for 30 minutes followed by addition of 1 g of 5-nitro furaldehyde in 7 mL of THF. The reaction medium is allowed to cool down to room temperature (ca. 20° C.) and then poured in a mixture of 200 mL of water and 100 mL of ethyl acetate (EtOAc). The organic layer is isolated and the aqueous layer is extracted twice with EtOAc (2×100 mL). The organic layers are combined, dried on magnesium sulfate, and concentrated under reduced pressure. 1.8 g of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is collected. Analytical LC/MS method B: RT: 2.98 min; [M+H]+: 259; 80% UV purity

Workup

temperatureat reflux temperature for 30 minutes
customThe organic layer is isolated
extractionthe aqueous layer is extracted twice with EtOAc (2×100 mL)
customdried on magnesium sulfate
concentrationconcentrated under reduced pressure
custom1.8 g of 5-(5-Methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde is collected

Sources & evidence

ORD record: ord-d20187fbfa2947a996056ed2350ec7c5
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163768B2

Reaction notes

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