Ammonia → 4-Bromo-2-fluorobenzimidamide hydrochloride

HRID 1800020Notes

Reaction equation

HRID 1800020 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-ce0003f87c7941ba8ba10d16dfc9ec3b
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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