Dimethylformamide → HCID 70098395, compound

HRID 2287333Notes

Reaction equation

HRID 2287333 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][N:8]([N:11]=CC2C=CC=CC=2)[C:7]1=[O:19].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:32][C:31]([CH:33]=O)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.CN(C)C=O>Cl.[Pd]>[ClH:21].[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[O:32][C:31]([CH:33]=[N:11][N:8]3[CH2:9][CH2:10][N:6]([CH2:5][CH2:4][CH2:3][N:2]([CH3:20])[CH3:1])[C:7]3=[O:19])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6761845-(4-Chlorophenyl)-2-furaldehydeHCID 53728677HCID 53728677, compound

Product 1

HCID 70098395HCID 70098395, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4.8 g (0.017 mole) of 3-[3-(dimethylamino) propyl]-1-[(phenylmethylene)amino]-2-imidazolidinone (prepared as described in Part III above) in 125 ml of 2 N HCl is treated with 1 g of 5% Pd/C (50% H20) and placed on the Parr reduction apparatus, with the theoretical amount of H2 being absorbed over a 30 minute period. The catalyst is removed by filtration and the solvent is removed in vacuo. The residual oil is dissolved in 100 ml of dimethylformamide and treated all at once with 3.51 g (0.0170 mole) of 5-(4-chlorophenyl)-2-furancarboxaldehyde (prepared as described in U.S. Pat. No. 4,882,354 to Huang et al., (issued Nov. 21, 1989), assigned to Norwich Eaton Pharmaceuticals, Inc., see Example 3, cols. 7 & 8, hereby incorporated by reference herein) with dissolution. A 1.0 g portion of 3 Angstrom molecular sieves is added and the reaction is stirred 16 to 18 hours at ambient temperature. The resulting mixture is heated to reflux with dimethylformamide being added to dissolution. The molecular sieves are removed by filtration and the solvent is removed in vacuo. The residual semi-solid is crystallized by trituration with ether. The solid is recrystallized from S.D.A. #32, (activated charcoal) and dried in a vacuum pistol over refluxing ethyl acetate to yield 2.7 g of 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3-(3-dimethylaminopropyl)-2-imidazolidinone hydrochloride.

Workup

  1. customabsorbed over a 30 minute period
  2. customThe catalyst is removed by filtration
  3. customthe solvent is removed in vacuo
  4. dissolutionThe residual oil is dissolved in 100 ml of dimethylformamide
  5. customprepared
  6. dissolution7 & 8, hereby incorporated by reference herein) with dissolution
  7. additionA 1.0 g portion of 3 Angstrom molecular sieves is added
  8. temperatureThe resulting mixture is heated
  9. additionadded to dissolution
  10. customThe molecular sieves are removed by filtration
  11. customthe solvent is removed in vacuo
  12. customThe residual semi-solid is crystallized by trituration with ether
  13. customThe solid is recrystallized from S.D.A
  14. dry with material#32, (activated charcoal) and dried in a vacuum pistol
  15. temperatureover refluxing ethyl acetate

Sources & evidence

ORD record
ord-da5e95d3cda04ed3bfd376e30c520011
Source dataset
uspto-grants-2000_07
Patent number
US06083945

Reaction notes

Loading…