Sodium Hydroxide → HCID 178429288, compound

HRID 1357285Notes

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][NH:17][C:18]([C:20]1[O:21][C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[C:24]=1[CH3:25])=[O:19])=[CH:7]2.[N-:30]=[N+:31]=[N-:32].[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:32][N:31]=[N:30][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][NH:17][C:18]([C:20]1[O:21][C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[C:24]=1[CH3:25])=[O:19])=[CH:7]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-methyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-amide (1.14 g, 2.54 mmol), prepared in the previous step, sodium azide (492 mg, 7.57 mmol) and ammonium chloride (406 mg, 7.59 mmol) in 50 mL of DMF was stirred under nitrogen at 100° C. for 5 h. By TLC starting material remained. An additional 494 mg (7.60 mmol) of sodium azide was added and the stirring continued at 100° C. for 2 h. The reaction was diluted with water, made basic by the addition of 1 N NaOH and extracted three times with ethyl acetate. The aqueous layer was acidified with 1 N HCl and the solid that precipitated was collected by filtration and dried under reduced pressure to give the title compound (987 mg, 79%) as a light brown solid, mp 212-215° C.

Workup

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

Sources & evidence

ORD record: ord-10bd6753ab4247ce872e10389d9cdf5a
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589970B2

Reaction notes

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