Water → HCID 25010451, compound

HRID 1471464Notes

Reaction equation

C([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[CH:5][CH:4]=1)#N.[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+].O.[CH3:27][N:28](C)C=O>>[OH:16][B:15]1[C:11]2[CH:10]=[CH:9][C:8]([O:7][C:6]3[CH:5]=[CH:4][C:3]([N:20]4[CH:27]=[N:28][N:22]=[N:21]4)=[CH:19][CH:18]=3)=[CH:17][C:12]=2[CH2:13][O:14]1

Participants

Reactant 5

HCID 962Water

HCID 6228Dimethylformamide

HCID 25517Ammonium Chloride

HCID 33557Sodium Azide

HCID 44591583AN2728

Product 1

HCID 25010451HCID 25010451, compoundYield 23%

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(4-cyanophenoxy)-1-hydroxy-2,1-benzoxaborole (200 mg, 0.797 mmol), sodium azide (103 mg, 1.59 mmol), and ammonium chloride (85 mg, 1.6 mmol) in N,N-dimethylformamide (5 mL) was stirred at 80° C. for two days. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) followed by trituration with ethyl acetate to give the target compound (55 mg, 23%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried on anhydrous sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-87e49869b6004dfda3beb3ff388e1ca9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012431B2

Reaction notes

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