Ammonia → 4-Bromo-2-fluorobenzimidamide hydrochloride

HRID 1498254Notes

Reaction equation

HRID 1498254 reaction equation
[ClH:1].C(O[C:5](=[NH:14])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[F:13])C.[NH3:15]>>[ClH:1].[Br:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]([NH2:14])=[NH:15])=[C:7]([F:13])[CH:8]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 670507354-Bromo-2-fluoro-benzimidic acid ethyl ester hydrochloride

Product 1

HCID 534078914-Bromo-2-fluorobenzimidamide hydrochlorideYield 100%

Procedure

A mixture of 4-bromo-2-fluoro-benzimidic acid ethyl ester hydrochloride (20.3 g, 72 mmol) in IMS (250 mL) at 0-5° C. was saturated with NH3 (gas), and the flask sealed before allowing to warm to RT and stirring for 18 h. Solvent was removed in vacuo and the residue triturated in diethyl ether to give 4-Bromo-2-fluoro-benzamidine hydrochloride as a white solid (18.1 g, 100%). 1H NMR δ (ppm) (DMSO-d): 9.26 (4H, s), 7.92-7.87 (1H, m), 7.71-7.62 (2H, m).

Workup

  1. customthe flask sealed
  2. customSolvent was removed in vacuo
  3. customthe residue triturated in diethyl ether

Sources & evidence

ORD record
ord-3c66818a578743d1a7498d210be84e0a
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

Loading…