Hydrochloric Acid → HCID 192455, compound

HRID 2211136Notes

Reaction equation

HRID 2211136 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][C:20]([CH:22]=[N:23][N:24]3[CH2:28][C:27](=[O:29])[N:26]([CH2:30][CH2:31][CH2:32]Cl)[C:25]3=[O:34])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+].[ClH:40]>CN(C)C=O>[ClH:10].[ClH:40].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:21][C:20]([CH:22]=[N:23][N:24]3[CH2:28][C:27](=[O:29])[N:26]([CH2:30][CH2:31][CH2:32][N:7]4[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]4)[C:25]3=[O:34])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76771-(2-Hydroxyethyl)piperazineHCID 516892Sodium BicarbonateHCID 70172843HCID 70172843, compound

Product 1

HCID 192455HCID 192455, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 4-(2-hydroxyethyl)piperazine (3.83 g, 0.03 mole) in AR grade dimethylformamide (130 ml) is treated with 1-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-3-(3-chloropropyl)-2,4-imidazolidinedione (6.92 g, 0.015 mole). The reaction solution is heated at near reflux for 1.5 hours and then concentrated under reduced pressure to leave an oily residue. Said residue is treated with saturated sodium bicarbonate solution to give a yellow mixture. The mixture is filtered and washed with water to give 3.92 g crude product as the free base. The solid is dissolved in alcohol and treated with a mixture of saturated ethanolic/HCl. The solution forms a crystalline solid after 5 minutes. The solid is collected by filtration to give the crude product. 1-[[[5-(4-Chlorophenyl)-2-furanyl]methylene]amino]-3-[3-[4-(2-hydroxyethyl)-1-piperazinyl]propyl]-2,4-imidazolidinedione dihydrochloride is isolated upon one recrystallization from 95% alcohol (2.57 g).

Workup

  1. temperatureThe reaction solution is heated
  2. temperatureat near reflux for 1.5 hours
  3. concentrationconcentrated under reduced pressure
  4. customto leave an oily residue
  5. customto give a yellow mixture
  6. filtrationThe mixture is filtered
  7. washwashed with water
  8. customto give 3.92 g crude product as the free base
  9. customafter 5 minutes
  10. filtrationThe solid is collected by filtration
  11. customto give the crude product

Sources & evidence

ORD record
ord-a6471271c22b4f72ab2122e9696ad893
Source dataset
uspto-grants-1995_10
Patent number
US05462940

Reaction notes

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