Sodium Hydroxide → HCID 178441996, compound

HRID 2355114Notes

Reaction equation

HRID 2355114 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH2:26][C:27]#[N:28])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].[N-:33]=[N+:34]=[N-:35].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[CH2:1]([C:5]1[O:6][C:7]2[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH2:26][C:27]2[NH:35][N:34]=[N:33][N:28]=2)[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride3×HCID 33557Sodium Azide3×HCID 68453947HCID 68453947, compound

Product 1

HCID 178441996HCID 178441996, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetonitrile (504 mg, 1.19 mmol), prepared in the previous step, sodium azide (230 mg, 3.54 mmol) and ammonium chloride (191 mg, 3.56 mmol) in 15 mL of DMF was stirred at 100° C. for 5 h. By TLC starting material remained. Additional sodium azide (230 mg, 3.54 mmol) and ammonium chloride (189 mg, 3.52 mmol) were added and the reaction stirred at 100° C. for two hours. Again by TLC starting material remained. Additional sodium azide (232 mg, 3.54 mmol) and ammonium chloride (191 mg, 3.55 mmol) were added and the reaction stirred at 100° C. for two hours. The reaction was diluted with water, made basic by the addition of 1N NaOH and extracted three times ethyl acetate The aqueous layer was acidified with 1N HCl. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (308 mg, 56%) as a white solid, mp 238-240° C. Elemental Analysis for C27H23N5O3 Calc'd: C, 69.66; H, 4.98; N, 15.04. Found: C, 69.51; H, 4.99; N, 15.1

Workup

  1. stirringthe reaction stirred at 100° C. for two hours
  2. stirringthe reaction stirred at 100° C. for two hours
  3. extractionextracted three times ethyl acetate The aqueous layer
  4. customThe solid that formed
  5. filtrationwas collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-79a72978566e444ba74fdaa895f6f9f9
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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