Water → 5-octyl-5-[N-(2-hydroxyethyl)piperazinyl]barbituric acid

HRID 993072Notes

Reaction equation

HRID 993072 reaction equation
Br[C:2]1([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>CS(C)=O>[CH2:11]([C:2]1([CH:23]2[CH2:24][NH:25][CH2:26][CH2:27][N:22]2[CH2:21][CH2:20][OH:19])[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 76771-(2-Hydroxyethyl)piperazineHCID 184088325-Bromo-5-octylbarbituric acid

Product 1

HCID 537770275-octyl-5-[N-(2-hydroxyethyl)piperazinyl]barbituric acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-Bromo-5-octylbarbituric Acid (23.52 g) in 70 ml of dimethylsulfoxide, kept under nitrogen atmosphere and at a temperature of 5-10° C., is dropped N-(2-hydroxyethyl)piperazine (36.2 ml), then the mixture is stirred at room temperature for 2 hours 30 minutes. The reaction mixture is poured into water (1 l) under stirring and cooling with an ice bath. The white solid which separates is recovered by filtration, washed with water and dried under vacuum at 40° C. to give, after crystallization from ethanol (140 ml) 10.91 g of the product as a white solid, m.p. 183-184° C.

Workup

  1. customkept under nitrogen atmosphere and at a temperature of 5-10° C.
  2. stirringunder stirring
  3. temperaturecooling with an ice bath
  4. filtrationThe white solid which separates is recovered by filtration
  5. washwashed with water
  6. customdried under vacuum at 40° C.
  7. customto give
  8. customafter crystallization from ethanol (140 ml) 10.91 g of the product as a white solid, m.p. 183-184° C.

Sources & evidence

ORD record
ord-5c76a301bf2b433191ebb84bd8384674
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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