Potassium Iodide → HCID 13469424, compound

HRID 2290272Notes

Reaction equation

HRID 2290272 reaction equation
Cl[CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]([CH3:20])[NH:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1.[I-].[K+].[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>CN(C=O)C.C(N(CC)CC)C>[O:4]1[CH2:27][CH2:28][N:23]([CH2:24][C:25]([NH:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[CH:14]([CH3:20])[NH:15][C:16](=[O:19])[NH:17][N:18]=3)=[CH:11][CH:12]=2)=[O:26])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6577Chloroacetyl chlorideHCID 8083MorpholineHCID 133860336-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one

Product 1

HCID 13469424HCID 13469424, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Chloroacetyl chloride (1.25 g) was added dropwise to a solution of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.04 g) and triethylamine (1.01 g) in DMF (10 ml) and then stirred for 30 minutes. To the stirred solution were added potassium iodide (0.53 g) and morpholine (4.53 g). The reaction mixture was stirred for 30 minutes and then evaporated in vacuo. To the residue was added water and the resultant solid was collected by filtration, washed with water and recrystallized from aqueous ethanol to give 6-[4-(2-morpholinoacetamido)phenyl]-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (2.13 g).

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. customevaporated in vacuo
  3. additionTo the residue was added water
  4. filtrationthe resultant solid was collected by filtration
  5. washwashed with water
  6. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-5c2864e07ca8489b9d03fc779e6de818
Source dataset
uspto-grants-1986_10
Patent number
US04616015

Reaction notes

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