Potassium Iodide → HCID 13469394, compound

HRID 2290266Notes

Reaction equation

HRID 2290266 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:6][CH:7]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 13469394HCID 13469394, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.04 g), 1,4-dibromobutane (2.59 g), potassium carbonate (0.35 g) and potassium iodide (0.5 g) in DMF (10 ml) was heated at 80° C. for 5 hours under stirring, and then evaporated in vacuo. After addition of 30% aqueous methanol to the residue, the resulting precipitates were collected by filtration and recrystallized from a mixture of methanol and chloroform (7:3) to give 6-(4-pyrrolidinophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (0.65 g).

Workup

  1. customevaporated in vacuo
  2. additionAfter addition of 30% aqueous methanol to the residue
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. customrecrystallized from a mixture of methanol and chloroform (7:3)

Sources & evidence

ORD record
ord-5ed0b772dea446dd97b7caafc2eace0f
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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