Benzamidine, hydrochloride → HCID 18673180, compound

HRID 1443539Notes

Reaction equation

HRID 1443539 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[O-].[Na+].Br[CH:15]([CH3:26])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=O>O1CCCC1>[C:3]1([C:2]2[NH:9][C:15]([CH3:26])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-oneHCID 10942334Sodium Methoxide2×

Product 1

HCID 18673180HCID 18673180, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A suspension of 47.3 g (0.302 mol) of benzamidine hydrochloride, 16.3 g (0.302 mol) of sodium methylate in 250 ml of tetrahydrofuran was heated under reflux for 1 hour, and cooled to 25° C. A solution of 85.2 g (0.302 mol) of the above-mentioned crude 2-bromo-2′,4′-dichloropropiophenone in 160 ml of tetrahydrofuran was added dropwise in such a manner that the reaction temperature did not exceed 30° C. After the addition was complete, 16.3 g (0.302 mol) of sodium methylate was added, and the resultant was heated under reflux for 1 hour. Subsequently, the reaction solution was cooled to room temperature, and insolubles were then filtered off. The filtrate was evaporated to dryness under reduced pressure, to recover a residual solid. This solid was successively washed with water and toluene and then dried, to give 50.4 g (55.0% crude yield) of crude crystals of the desired product. The crude crystals were recrystallized using a mixture of acetonitrile and DMF, to give colorless purified crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customdid not exceed 30° C
  4. additionAfter the addition
  5. temperaturethe resultant was heated
  6. temperatureunder reflux for 1 hour
  7. temperatureSubsequently, the reaction solution was cooled to room temperature
  8. filtrationinsolubles were then filtered off
  9. customThe filtrate was evaporated to dryness under reduced pressure
  10. customto recover a residual solid
  11. washThis solid was successively washed with water and toluene
  12. customdried

Sources & evidence

ORD record
ord-2eb2f54aae2f44839ae1a8c7a7bdbd6f
Source dataset
uspto-grants-2010_02
Patent number
US07661577B2

Reaction notes

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