Potassium Iodide → HCID 21450910, compound

HRID 596398Notes

Reaction equation

HRID 596398 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[C:20]([CH2:21][N:22]([CH3:24])[CH3:23])=[N:19][N:18]=[C:17]2[CH2:25]O)=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].CS(Cl)(=O)=O.[CH2:32]([NH2:35])[CH:33]=[CH2:34].[I-].[K+].[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[C:20]([CH2:21][N:22]([CH3:24])[CH3:23])=[N:19][N:18]=[C:17]2[CH2:25][NH:35][CH2:32][CH:33]=[CH2:34])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 7853AllylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 21450879[5-Chloro-2-[3-[(dimethylamino)methyl]-5-(hydroxymethyl)-4H-1,2,4-triazol-4-yl]phenyl]phenylmethanone

Product 1

HCID 21450910HCID 21450910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.01 g. (3.00 mmole) of 5-chloro-2-[3-(hydroxymethyl)-5-[(dimethylamino)methyl]-4H-1,2,4-triazol-4-yl]benzophenone in 15 ml. of methylene chloride and cooled to 0° C. is treated dropwise with 0.378 g. (3.30 mmole) of methane sulfonylchloride. The mixture is stirred for 1/2 hour, poured onto ice, and extracted with a saturated aqueous sodium bicarbonate solution. The organic layer is removed, dried with anhydrous sodium sulfate and concentrated in vacuo to an oil. This resulting oil, dissolved in 20 ml. of tetrahydrofuran, is treated with 0.56 g. (10 mmole) of allylamine and 0.996 g. (6.0 mmole) of potassium iodide and heated to reflux for 24 hours. The reaction mixture is poured onto a cold (0°-5° C.) 10% aqueous sodium hydroxide solution and extracted with chloroform. The chloroform extract is dried with anhydrous sodium sulfate and concentrated in vacuo to give 5-chloro-2-[3-[(allylamino)methyl]-5-[(dimethylamino)methyl]-4H-1,2,4-triazol-4-yl]benzophenone.

Workup

  1. additionis treated dropwise with 0.378 g
  2. additionpoured onto ice
  3. extractionextracted with a saturated aqueous sodium bicarbonate solution
  4. customThe organic layer is removed
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to an oil
  7. dissolutionThis resulting oil, dissolved in 20 ml
  8. additionof tetrahydrofuran, is treated with 0.56 g
  9. temperatureto reflux for 24 hours
  10. extractionextracted with chloroform
  11. extractionThe chloroform extract
  12. dry with materialis dried with anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-782e716cb0b84e949ccf0e9eb69e1089
Source dataset
uspto-grants-1977_03
Patent number
US04010177

Reaction notes

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