Tetrahydrofuran → HCID 178420134, compound

HRID 389227Notes

Reaction equation

HRID 389227 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+].O1[CH2:18][CH2:17][CH2:16][CH2:15]1>>[C:3]1([C:2]2[NH:9][CH:15]=[C:16]([C:17]3[CH:18]=[CH:5][C:4]4[C:16](=[CH:17][CH:18]=[CH:2][CH:3]=4)[CH:15]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 80289Benzamidine, hydrochlorideHCID 10942334Sodium Methoxide2×

Product 1

HCID 178420134HCID 178420134, compound

Conditions

Temperature
20 °C

Procedure

A suspension consisting of 31.3 g (0.20 mol) of benzamidine hydrochloride, 10.8 g (0.20 mol) of sodium methylate, and 150 mL of tetrahydrofuran was heated under reflux for one hour. After cooling to 20° C., a solution consisting of 49.8 g (0.2 mol) of ω-bromo-2-acetonaphthone and 100 mL of tetrahydrofuran was added dropwise such that the internal temperature did not exceed 30° C. After completion of addition, 10.8 g (0.20 mol) of sodium methylate was added, and the mixture was heated under reflux for one hour. Next, the reaction mixture was cooled to room temperature, insoluble matters were filtered off, and the filtrate was evaporated to dryness in vacuo. The residual solid was successively washed with water and toluene and then dried to obtain a crude crystal as a desired material. This crude crystal was recrystallized from acetonitrile to obtain 32.8 g (yield: 60.7%) of a colorless crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. additionwas added dropwise such that the internal temperature
  4. customdid not exceed 30° C
  5. additionwas added
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for one hour
  8. temperatureNext, the reaction mixture was cooled to room temperature
  9. filtrationinsoluble matters were filtered off
  10. customthe filtrate was evaporated to dryness in vacuo
  11. washThe residual solid was successively washed with water and toluene
  12. customdried

Sources & evidence

ORD record
ord-279e41ef6d644b519eb02978146dff68
Source dataset
uspto-grants-2013_02
Patent number
US08378116B2

Reaction notes

Loading…