Ammonia → 4-Bromo-2-fluorobenzimidamide hydrochloride

HRID 1629221Notes

Reaction equation

HRID 1629221 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 (4 H, s), 7.92-7.87 (1 H, m), 7.71-7.62 (2 H, m).

Workup

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

Sources & evidence

ORD record
ord-a4d538946fa440e8a57ce5f6fc2ce2d4
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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