Benzamidine, hydrochloride → HCID 23103026, compound

HRID 1443541Notes

Reaction equation

HRID 1443541 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=O.Cl.[C:15]([NH2:23])(=[NH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[K+]>O1CCCC1.O>[C:16]1([C:15]2[NH:22][C:2]([CH3:13])=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=3)[N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 516893Potassium BicarbonateHCID 134353622-Bromo-1-(3,4-dichlorophenyl)propan-1-one

Product 1

HCID 23103026HCID 23103026, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 86.6 g (0.307 mol) of the above-mentioned crude 2-bromo-3′,4′-dichloropropiophenone in 120 ml of tetrahydrofuran was added dropwise over 40 minutes into a suspension, under reflux with heating, of 48.1 g (0.307 mol) of benzamidine hydrochloride, 123.4 g (1.23 mol) of potassium bicarbonate in 450 ml of tetrahydrofuran and 110 ml of water. After the addition was complete, further refluxing with heating was carried out for 2 hours. The reaction solution was evaporated to dryness under reduced pressure, to give a residual solid. This solid was successively washed with water and toluene, to give 65.3 g (71.3% crude yield) of crude crystals of the desired product. The crude crystals were recrystallized using acetonitrile, to give a purified white powder.

Workup

  1. temperatureunder reflux
  2. additionAfter the addition
  3. temperaturefurther refluxing
  4. temperaturewith heating
  5. customThe reaction solution was evaporated to dryness under reduced pressure
  6. customto give a residual solid
  7. washThis solid was successively washed with water and toluene

Sources & evidence

ORD record
ord-47b2d3aab91742729d1545a58d8f1383
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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