1-Chloro-4-nitrobenzene → 2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole

HRID 1057089Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]3=[N:11]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-chloronitrobenzene (55.0 g, 349 mmol), benzotriazole (50.0 g, 420 mmol), potassium carbonate (200 g, 500 mmol), and NMP (500 mL) was stirred and heated under argon at 130° C. for 5 hours. Progress of the reaction was monitored by thin layer chromatography. The reaction mixture was poured onto crushed ice (2 kg). After all ice melted, the solid was filtered off and washed with water (200 mL). The product was suspended in methanol (1.5 L) and stirred for 30 minutes. The crystals were filtered off and dried in a vacuum oven. Column chromatography of the obtained material using silica gel and hot solution of ethyl acetate (1%) in toluene as an eluent gave 2-(4-nitrophenyl)-2H benzo[d][1,2,3]triazole (24.24 g, 30% yield). 1H NMR (400 MHz, CDCl3): δ 8.57 (d, J=9.2 Hz, 2H, 4-nitrophenyl), 8.44 (d, J=9.2 Hz, 2H, 4-nitrophenyl), 7.93 (m, 2H, benzotriazole), 7.47 (m, 2H, benzotriazole).

Workup

additionThe reaction mixture was poured
filtrationthe solid was filtered off
washwashed with water (200 mL)
stirringstirred for 30 minutes
filtrationThe crystals were filtered off
customdried in a vacuum oven

Sources & evidence

ORD record: ord-91688649c01d437a95926157bd738bce
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399730B2

Reaction notes

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