Sodium Hydroxide → HCID 178442004, compound

HRID 1357252Notes

Reaction equation

[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]#[N:15])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:33])[C:18]([C:20]1[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH2:29][CH2:30][CH2:31][CH3:32])=[O:19])=[CH:7]2.[N-:34]=[N+:35]=[N-:36].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[NH:36][N:35]=[N:34][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:33])[C:18]([C:20]1[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH2:29][CH2:30][CH2:31][CH3:32])=[O:19])=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.3 g, 0.59 mmol), prepared in the previous step, sodium azide (0.116 g, 1.78 mmol) and ammonium chloride (0.095 g, 1.78 mmol) in 12 mL DMF was stirred under nitrogen at 100° C. for 6.5 h. The reaction was diluted with water, made basic with 1N NaOH, and extracted three times with ethyl acetate. The organic layers were combined, acidified with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give an oily residue. The oil was diluted with water and the solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (0.20 g, 63%) as an off white solid, mp 190-194° C.

Workup

extractionextracted three times with ethyl acetate
dry with materialdried (MgSO4)
customthe solvent removed under reduced pressure
customto give an oily residue
customthe solid that formed
filtrationwas collected by filtration
washrinsed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-2505663f79ea4223ab5df0381e5fd3aa
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589970B2

Reaction notes

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