Sodium Hydroxide → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzotriazole

HRID 74195Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([NH:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:14]([CH:16]=1)[NH2:15].[N:24]([O-])=O.[Na+].[OH-].[Na+]>Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]2[N:17]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:24]=[N:15][C:14]=2[CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.35 g, 1.13 mmol) in concentrated hydrochloric acid (2 mL) was added dropwise an aqueous solution containing sodium nitrite (0.09 g, 1.24 mmol) with cooling to 0° C. After stirring for 2 hours at room temperature, this was cooled to 0° C. and was made alkaline with 1N aqueous sodium hydroxide solution, then extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to yield the title compound (0.17 g, 46.9% yield) as dark brown crystals.

Workup

temperaturethis was cooled to 0° C.
extractionextracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-bc952e900d23436daf819db1c5c90afd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829035B2

Reaction notes

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