Hydrochloric Acid → HCID 44594093, compound

HRID 2105180Notes

Reaction equation

N([O-])=O.[Na+].O.Cl.[CH2:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[NH:21][NH:22][C:23]([C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)=[N:24][N:25]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[CH2:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[N:21]=[N:22][C:23]([C:26]2[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=2)=[N:24][N:25]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6N NaNO2 in water (1 mL, 5.876 mmol) was added dropwise to conc. HCl (0.7 mL, 7.05 mmol). The resulting nitrous gases were bubbled through a suspension of 22 (200 mg, 0.588 mmol) in CH2Cl2 cooled to 0° C. for 1 hr. The solvent was removed in vacuo. The purple residue was purified by flash column chromatography (2% EtOAc in n-hexane) to give 3-(2-Benzyl-phenyl)-6-m-tolyl-[1,2,4,5] tetrazine 23 (198 mg, 0.585 mmol, 100% yield). m.p. 90-91° C.; HRMS (MALDI-FTMS) calcd for C22H18N4+H+: 339.1604, found 339.1597.

Workup

customThe solvent was removed in vacuo
customThe purple residue was purified by flash column chromatography (2% EtOAc in n-hexane)

Sources & evidence

ORD record: ord-2f8066547d3243d9927930d99c45d58e
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579350B2

Reaction notes

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