Benzamidine, hydrochloride → HCID 178477950, compound

HRID 1443537Notes

Reaction equation

HRID 1443537 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=O.Cl.[C:14]([NH2:22])(=[NH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[K+]>O1CCCC1.O>[C:15]1([C:14]2[NH:21][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=3)[N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 516893Potassium Bicarbonate

Product 1

HCID 178477950HCID 178477950, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 68.0 g (0.254 mol) of the above-mentioned crude 2-bromo-3′,4′-dichloroacetophenone in 110 ml of tetrahydrofuran was added dropwise over 30 minutes, under reflux with heating, into a suspension of 39.8 g (0.254 mol) of benzamidine hydrochloride, 102.1 g (1.02 mol) of potassium bicarbonate in 400 ml of tetrahydrofuran and 100 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 45.5 g (62.0% 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-4ce33d2532c2474581d5dea9658dc687
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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