Water → HCID 53714502, compound

HRID 1283463Notes

Reaction equation

HRID 1283463 reaction equation
[C:1]([C:6]1[C:7]([N:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)=[N:8][C:9](Cl)=[N:10][C:11]=1[CH3:12])([O:3][CH2:4][CH3:5])=[O:2].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>O1CCOCC1>[C:1]([C:6]1[C:7]([N:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)=[N:8][C:9]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[N:10][C:11]=1[CH3:12])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 54025792HCID 54025792, compound

Product 1

HCID 53714502HCID 53714502, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 gm (0.006 mol) of 5-carbethoxy-2-chloro-4-(1,1-dioxido-thiomorpholino)-6-methyl-pyrimidine were added in small portions to a boiling solution of 5.2 gm (0.06 mol) of piperazine in 70 ml of dioxane, and the mixture was refluxed for 20 minutes. The reaction mixture was then poured into 150 ml of water, and the aqueous mixture was extracted with chloroform. The organic extract was washed with water, dried with sodium sulfate, and the solvent was removed in vacuo. The residue was recrystallized from ethanol/petroleum ether. Yield: 1.7 gm (74% of theory); m.p. 154°-159°C.

Workup

  1. temperaturethe mixture was refluxed for 20 minutes
  2. extractionthe aqueous mixture was extracted with chloroform
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried with sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was recrystallized from ethanol/petroleum ether

Sources & evidence

ORD record
ord-bc88a4f061a849258ab89cbd49d170a2
Source dataset
uspto-grants-1976_08
Patent number
US03975384

Reaction notes

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