Sodium Hydroxide → HCID 178429305, compound

HRID 1357283Notes

Reaction equation

HRID 1357283 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]([CH3:30])[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-:31]=[N+:32]=[N-:33].[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:33][N:32]=[N:31][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:16][N:17]([CH3:30])[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

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12083578HCID 12083578, compound

Product 1

HCID 178429305HCID 178429305, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.039 g, 4.40 mmol), prepared in the previous step, sodium azide (846 mg, 13.0 mmol) and ammonium chloride (695 mg, 13.0 mmol) in 60 mL of DMF was stirred under nitrogen at 100° C. for 6 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, which caused an oil to precipitate. The aqueous layer was decanted from the oil. Water was added to the oil, which caused it to solidify. The solid was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound as a white solid, mp 164-166° C.

Workup

  1. extractionextracted three times with ethyl acetate
  2. customto precipitate
  3. customThe aqueous layer was decanted from the oil
  4. additionWater was added to the oil, which
  5. filtrationThe solid was collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-d65714195bb340bd9b5211d69102b86c
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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