Benzyl Alcohol → 5-benzyloxy-N,N-dimethyl-2-nitrobenzamide

HRID 2114177Notes

Reaction equation

[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:12]1[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([CH:22]=1)[C:17]([N:19]([CH3:21])[CH3:20])=[O:18]>CN(C=O)C>[CH2:3]([O:10][C:12]1[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([CH:22]=1)[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (210 mg) was suspended in DMF (10 mL), and the suspension was cooled to 0° C. and thereto were added benzyl alcohol (568 mg) and a solution of 5-chloro-N,N-dimethyl-2-nitrobenzamide (1.00 g) in DMF (2 mL). The mixture was stirred at 50° C. for 0.5 hour and then concentrated. The residue was acidified with 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:3) to give 5-benzyloxy-N,N-dimethyl-2-nitrobenzamide (1.18 g)

Workup

concentrationconcentrated
extractionextracted with ethyl acetate
washThe extract was washed with water
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2→2:3)

Sources & evidence

ORD record: ord-fc65824a0cfa40f8a7587440764e6c86
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432392B2

Reaction notes

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