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

HRID 1872575Notes

Reaction equation

HRID 1872575 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-61ce5a1612b04c5b89e71c232e8f0543
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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