Hydrochloric Acid → HCID 13216719, compound

HRID 2283138Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[N-:13]=[N+:14]=[N-:15].[Na+].Cl>CC(O)C.O.[Br-].[Zn+2].[Br-]>[N+:10]([C:3]1[CH:4]=[C:5]([C:6]2[N:13]=[N:14][NH:15][N:7]=2)[CH:8]=[CH:9][C:2]=1[NH2:1])([O-:12])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-amino-3-nitrobenzonitrile (4.98 g, 36 mol) in 2-propanol (15 ml) and water (30 ml) was added zinc bromide (13.80 g, 61 mmol) followed by sodium azide (5.81 g, 89 mmol). The reaction mixture was at heated at 80° C. for 10 hours. The reaction was cooled and then analyzed by HPLC. Water (15 ml) was added and the orange colored mixture adjusted to pH 3.0 with 50% (v/v) HCl. The solid was washed with water (50 ml) and dried in an oven at 90° C. to yield an orange yellow colored solid 2-nitro-4-(2H-tetrazol-5-yl)-phenylamine (6.59 g), Rt=8.8 mins, 1H NMR (d6-DMSO, 400 MHz) 8.47 ppm (1H, d, 2 Hz), 7.86 ppm (1H, d of d, 9 Hz, 2 Hz), 7.58 ppm (2.3H bs), 6.96 ppm (1H d, 9 Hz). MS (Electrospray+) 206 m/z (M+), 228 m/z (M+Na).

Workup

temperatureThe reaction was cooled
washThe solid was washed with water (50 ml)
customdried in an oven at 90° C.

Sources & evidence

ORD record: ord-566685ff51114816b5a4df0164abdcbc
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09144757B2

Reaction notes

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