Nitric Acid → HCID 178493228, compound

HRID 1855330Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:15])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[N:16]#[C:17][NH2:18].[N+:19]([O-:22])([OH:21])=[O:20]>C(O)C.O.Cl>[N+:19]([O-:22])([OH:21])=[O:20].[N+:19]([O-:22])([OH:21])=[O:20].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:17]([NH2:18])=[NH:16])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (5.08 g, 25.0 mmol) in ethanol (25 mL) was added at 20° C. cyanamide (3.15 g, 75 mmol) dissolved in water (3.2 mL) and then 37% aqueous hydrochloric acid solution (4.9 g, 50 mmol). The solution was heated for 3 h to reflux. Additional cyanamide (2.1 g) in water (2.1 mL) and 37% aq hydrochloric acid solution (2.8 mL) were added and the mixture was heated to reflux for another 2 h. At 20° C. 65% aqueous nitric acid (3.5 mL, 50 mmol) was added. The reaction was stirred for 30 minute at 20° C. and the formed precipitate was filtered off, washed with ethanol and diethyl ether. (Caution: the filtrate may contain the ethyl ester of nitric acid). The solid was dried under reduced pressure at 20° C. to yield the title compound (5.42 g, 58%) as a white solid.

Workup

temperatureThe solution was heated for 3 h
temperatureto reflux
temperaturethe mixture was heated
temperatureto reflux for another 2 h
customAt 20° C
filtrationthe formed precipitate was filtered off
washwashed with ethanol and diethyl ether
customThe solid was dried under reduced pressure at 20° C.

Sources & evidence

ORD record: ord-d076bd2e2f104317994435eeef79f5da
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962834B2

Reaction notes

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