5-(4-Chlorophenyl)-2-furaldehyde → HCID 70098637, compound

HRID 2287338Notes

Reaction equation

HRID 2287338 reaction equation
C1(C=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[C:10]2=[O:19])C=CC=CC=1.C1(C=NN2CCN(CCCCI)C2=O)C=CC=CC=1.[H][H].[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[O:52][C:51]([CH:53]=O)=[CH:50][CH:49]=2)=[CH:44][CH:43]=1>Cl.[Pd].CN(C)C=O>[ClH:41].[Cl:41][C:42]1[CH:43]=[CH:44][C:45]([C:48]2[O:52][C:51]([CH:53]=[N:8][N:9]3[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]([CH3:17])[CH3:18])[C:10]3=[O:19])=[CH:50][CH:49]=2)=[CH:46][CH:47]=1

Participants

8

Reactant 4

HCID 6761845-(4-Chlorophenyl)-2-furaldehydeHCID 57037835HCID 57037835, compoundHCID 57312351HCID 57312351, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70098637HCID 70098637, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-phenylmethyleneamino-3-[2-(dimethylamino) ethyl]-2-imidazolidinone, prepared as described in Part II above (6.17 g, 0.023 mole) in 2 N HCl (166 ml) is treated with 5% palladium on carbon (50% wet catalyst) (1.3 g). The reaction mixture is reduced on Parr apparatus under hydrogen. The hydrogen uptake stopped after 1/2 hour with 100% of theoretical uptake observed. The catalyst is removed and the filtrate concentrated under reduced pressure to leave a white residue. The residue is treated with a solution of 5-(4-chlorophenyl)-2-furancarboxaldehyde (prepared as described in U.S. Pat. No. 4,882,354 to Huang et al., assigned to Norwich Eaton Pharmaceuticals, Inc., issued Nov. 21, 1989, see Example 3, cols. 7, 8, hereby incorporated by reference herein) (4.81 g, 0.023 mole) in dry dimethylformamide (137 ml). The reaction is stirred at ambient temperature overnight. The reaction mixture is filtered and washed with anhydrous ether to give 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3-[2-(dimethyl amino)ethyl]-2-imidazolidinone hydrochloride.

Workup

  1. customprepared
  2. customThe catalyst is removed
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto leave a white residue
  5. customprepared
  6. filtrationThe reaction mixture is filtered
  7. washwashed with anhydrous ether

Sources & evidence

ORD record
ord-80df0c7880f942fcb50eb740f070ca62
Source dataset
uspto-grants-2000_07
Patent number
US06083945

Reaction notes

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