Sodium Hydroxide → HCID 178442006, compound

HRID 1357298Notes

Reaction equation

HRID 1357298 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]([CH2:33][CH2:34][CH2:35][CH3:36])[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-:37]=[N+:38]=[N-:39].[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:39][N:38]=[N:37][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH2:33][CH2:34][CH2:35][CH3:36])[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

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 12083588HCID 12083588, compound

Product 1

HCID 178442006HCID 178442006, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-butyl-amide (0.285 g, 0.52 mmol), prepared in the previous step, sodium azide (0.101 g, 1.56 mmol) and ammonium chloride (0.083 g, 1.56 mmol) in 10 mL of anhydrous DMF was stirred at 100° C. under nitrogen for 5 h. By TLC starting material remained. Additional amounts of sodium azide (0.101 g, 1.56 mmol) and ammonium chloride (0.083 g, 1.56 mmol) were added and the reaction stirred at 100° C. under nitrogen for 3 h. The reaction was diluted with water, made basic with 1N NaOH and extracted five times with ethyl acetate. The organic layer was separated and acidified with 1N HCl. The solvent was removed under reduced pressure and the residue diluted with 10 mL of water. A solid foam formed, which was collected by filtration and dried under reduced pressure to give the title compound (0.2765 g, 90%) as a tan foam, MS m/z: 588 [M−H]−.

Workup

  1. stirringthe reaction stirred at 100° C. under nitrogen for 3 h
  2. extractionextracted five times with ethyl acetate
  3. customThe organic layer was separated
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue diluted with 10 mL of water
  6. customA solid foam formed
  7. filtrationwhich was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-962290402ec44217ab42c5c24bd13081
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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