Hydrochloric Acid → HCID 178420075, compound

HRID 456821Notes

Reaction equation

[C:1]1([C:7]2[NH:11][C:10]([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:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].[N-:28]=[N+:29]=[N-:30].[Na+].Cl>O>[C:1]1([C:7]2[NH:11][C:10]([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:30][N:29]=[N:28][N:25]=3)[CH:16]=[CH:15]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of {[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetonitrile (0.20 g, 0.62 mmol), prepared in the previous step, ammonium chloride (0.12 g, 1.85 mmol) and sodium azide (0.099 g, 1.85 mmol) in DMIF (10 mL) was heated at 100° C. under nitrogen for 5 hours. After cooling to ambient temperature, TLC analysis showed that starting material remained. An additional portion each of ammonium chloride and sodium azide was added, and the mixture was again heated at 100° C. for 4 hours, at which time no starting material remained. The mixture was cooled to ambient temperature, acidified with 1N HCl (5 mL) and diluted with water (20 mL). The precipitated solids were isolated by vacuum filtration to give the title compound as a gray solid (0.202 g, 89%), mp 237–240° C. (dec). Elemental Analysis for C22H17N5O.0.55 H2O.0.11 C3H7NO Calc'd: C, 69.60; H, 4.94; N, 18.57. Found: C, 69.71; H, 4.64; N, 18.61.

Workup

temperatureAfter cooling to ambient temperature
temperaturethe mixture was again heated at 100° C. for 4 hours, at which time no starting material
temperatureThe mixture was cooled to ambient temperature
customThe precipitated solids were isolated by vacuum filtration

Sources & evidence

ORD record: ord-c7016094e1d3460098026fc7027558d2
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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