Sodium Hydroxide → HCID 178482588, compound

HRID 1357288Notes

Reaction equation

HRID 1357288 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]([CH3:37])[C:18]([C:20]1[O:21][C:22]3[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=3[C:24]=1[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:19])=[CH:7]2.[N-:38]=[N+:39]=[N-:40].[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:40][N:39]=[N:38][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:37])[C:18]([C:20]1[O:21][C:22]3[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=3[C:24]=1[CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:19])=[CH:7]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium Azide2×HCID 12083582HCID 12083582, compound

Product 1

HCID 178482588HCID 178482588, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-phenylethyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.29 g, 4.15 mmol), prepared in the previous step, sodium azide (808 mg, 12.4 mmol) and ammonium chloride (668 mg, 12.5 mmol) in 50 mL of DMF was stirred under nitrogen at 100° C. for 5 h. By TLC starting material remained. An additional 801 mg (12.3 mmol) of sodium azide was added and the reaction stirred at 100° C. overnight. The reaction was diluted with 50 mL of 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. An oil precipitated. The aqueous layer was decanted and the oil partitioned between methylene chloride and water. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give the title compound as a light brown solid, mp 56-59° C.

Workup

  1. stirringthe reaction stirred at 100° C. overnight
  2. extractionextracted three times with ethyl acetate
  3. customAn oil precipitated
  4. customThe aqueous layer was decanted
  5. customthe oil partitioned between methylene chloride and water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ba9e68288855452eb944185bb88418b7
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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