Ammonia → 3-(3-Bromo-4-fluorophenyl)propanimidamide hydrochloride

HRID 474555Notes

Reaction equation

HRID 474555 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8].CO.C([Cl:18])(=O)C.[NH3:19]>C1(C)C=CC=CC=1>[ClH:18].[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11](=[NH:19])[NH2:12])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 6367Acetyl chlorideHCID 534343013-(3-Bromo-4-fluorophenyl)propanenitrile

Product 1

HCID 677757593-(3-Bromo-4-fluorophenyl)propanimidamide hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-(3-bromo-4-fluorophenyl)propanenitrile (5.0 g, 21.05 mmol) in toluene (20 mL) and methanol (6.32 mL, 156 mmol) at 0° C. was added acetyl chloride (7.51 mL, 105 mmol) dropwise over 5 min. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was cooled to 0° C. by an ice bath, to which ammonia (30.1 mL, 210 mmol) was added dropwise. The reaction mixture was stirred at room temperature overnight. The mixture was filtered, and the filtrate was concentrated to give a crude product. Recrystallization from toluene/methanol (1:1) then afforded the title compound as a white solid (5.2 g, 93% yield). LCMS: rt=1.18 min, [M+H+]=245

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give a crude product
  6. customRecrystallization from toluene/methanol (1:1)

Sources & evidence

ORD record
ord-c466bac0dd324917b99b21f04c248937
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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