Nitric Acid → HCID 178429954, compound

HRID 1855351Notes

Reaction equation

HRID 1855351 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:14])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1.[N:15]#[C:16][NH2:17].[N+:18]([O-:21])([OH:20])=[O:19]>C(O)C>[N+:18]([O-:21])([OH:20])=[O:19].[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:16]([NH2:17])=[NH:15])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 9864Cyanamide2×HCID 218766383-Fluoro-4-(4-methyl-1H-imidazol-1-yl)aniline

Product 1

HCID 178429954HCID 178429954, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 3-fluoro-4-(4-methyl-imidazol-1-yl)-phenylamine (500 mg, 2.62 mmol), of 50% aqueous cyanamide solution (249 mg, 2.96 mmol) and of 65% aqueous nitric acid (253 mg, 2.62 mmol) in ethanol (2.6 mL) was heated for 5 days to reflux under an atmosphere of nitrogen. Twice the same amounts of cyanamide and nitric acid were added to the reaction mixture after 2 and 4 days, respectively. The mixture was cooled and let stand at 20° C. for 1 d. The precipitated solid was filtered off (Caution: the filtrate may contain the ethyl ester of nitric acid) and washed with ethanol to yield the title compound (280 mg, 36%) as an off-white solid.

Workup

  1. temperatureto reflux under an atmosphere of nitrogen
  2. temperatureThe mixture was cooled
  3. filtrationThe precipitated solid was filtered off (Caution
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-fa22695ede1a4e439d6e3e7d4d015a98
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

Loading…