Hydrochloric Acid → HCID 13216719, compound

HRID 1427318Notes

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-85941d8885a041dab308fe556daa0a1d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933206B2

Reaction notes

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