Sodium Hydroxide → HCID 178441201, compound

HRID 1357281Notes

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[O:21][C:22]3[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=3[C:24]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[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[O:21][C:22]3[CH:32]=[CH:31][CH:30]=[CH:29][C:23]=3[C:24]=1[CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-butyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (1.90 g, 3.77 mmol), prepared in the previous step, sodium azide (735 mg, 11.3 mmol) and ammonium chloride (607 mg, 11.3 mmol) in 50 mL of DMF was stirred under nitrogen at 100° C. for 5 h. By TLC starting material remained. An additional 732 mg (11.3 mmol) of sodium azide was added and the stirring continued at 100° C. for 2 h. The reaction was diluted with 50 mL of water, made basic by the addition of 1 N NaOH and then extracted three times with ethyl acetate. The aqueous layer was acidified with 1 N HCl and the solid that formed was collected by filtration and dried under reduced pressure to give the title compound (1.17 g, 57%) as a light brown solid, mp 180-183° C.

Workup

waitthe stirring continued at 100° C. for 2 h
extractionextracted three times with ethyl acetate
customthe solid that formed
filtrationwas collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-e7b42c70ee2e4f07b0f6637cd082f691
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589970B2

Reaction notes

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