Sodium Hydroxide → HCID 178420144, compound

HRID 2355110Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of {[6-(2-phenyl-1,3-oxazol-5-yl)-2-naphthyl]oxy} acetonitrile (187 mg, 0.574 mmol), prepared in the previous step, sodium azide (113 mg, 1.74 mmol) and ammonium chloride (92.7 mg, 1.73 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 4.5 h. The reaction was diluted with 10 mL of water, made basic by the addition of 1 mL of 1 N NaOH and extracted five times with ethyl acetate. The aqueous layer was acidified by the addition of 1 N HCl. The solid that precipitated was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (145 mg, 65%) as an off-white solid, mp 239-241° C. Elemental Analysis for C21H15N5O2+0.44 H2O: Calc'd: C, 66.85; H, 4.24; N, 18.56. Found: C, 66.36; H, 4.34; N, 18.41.

Workup

extractionextracted five times with ethyl acetate
additionThe aqueous layer was acidified by the addition of 1 N HCl
customThe solid that precipitated
filtrationwas collected by filtration
washrinsed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-d4c1cbd4cfd84e659e42a77be5f3cb4e
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754747B2

Reaction notes

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