Sodium Hydroxide → HCID 178434813, compound

HRID 1357236Notes

Reaction equation

HRID 1357236 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[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH3:29])=[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[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][C:21]=1[CH3:29])=[O:19])=[CH:7]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12083560HCID 12083560, compound

Product 1

HCID 178434813HCID 178434813, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-methyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-amide (233 mg, 0.52 mmol), prepared in the previous step, sodium azide (101 mg, 1.56 mmol) and ammonium chloride (83 mg, 1.55 mmol) in 15 mL of DMF was stirred under nitrogen at 100° C. for 8 h. The reaction was diluted with 35 mL of water, made basic by the addition of 3 mL of 1 N NaOH and extracted five times with ethyl acetate. The aqueous layer was acidified by the addition of 5 mL of 1 N HCl. The solid that precipitated was collected by filtration and dried under reduced pressure to give the title compound (216 mg, 85%) as a white solid, mp 242-244° C.

Workup

  1. extractionextracted five times with ethyl acetate
  2. additionThe aqueous layer was acidified by the addition of 5 mL of 1 N HCl
  3. customThe solid that precipitated
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-89f3c0120e0244a0bc05147e656e9c36
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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