Sodium Hydroxide → HCID 10229771, compound

HRID 1357220Notes

Reaction equation

HRID 1357220 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]([NH:16][C:17]([C:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][C:20]=1[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])=[CH:7]2.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[C:11]([O:12][CH2:13][C:14]2[N:32]=[N:33][NH:34][N:15]=2)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:16][C:17]([C:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][C:20]=1[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])=[CH:7]2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12083559HCID 12083559, compound

Product 1

HCID 10229771HCID 10229771, compoundYield 72.5%

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-yl)-amide (266 mg, 0.557 mmol), prepared in the previous step, sodium azide (110 mg, 1.69 mmol) and ammonium chloride (90.2 mg, 1.69 mmol) in 15 ml of DMF was stirred under nitrogen at 100° C. for 5 h. The reaction was diluted with water, made basic with 1 N NaOH and extracted five times with ethyl acetate. The ethyl acetate extract was acidified with 1 N HCl, filtered and the solvent concentrated under reduced pressure and then diluted with water. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (210 mg, 72%) as an off-white solid, mp 242-245° C.

Workup

  1. extractionextracted five times with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. filtrationfiltered
  4. concentrationthe solvent concentrated under reduced pressure
  5. additiondiluted with water
  6. filtrationThe solid present was collected by filtration
  7. washrinsed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-e2e87e626fc744659c3fdd5741658bc5
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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