Acetyl chloride → HCID 11793343, compound

HRID 359693Notes

Reaction equation

HRID 359693 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:25]([CH3:27])[CH3:26])=[N:10][CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[C:13]2[S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:25]([CH3:27])[CH3:26])=[N:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 105680931-(5-Amino-2-pyridyl)-2-(2-(dimethylamino)benzylthio)imidazole

Product 1

HCID 11793343HCID 11793343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.26 ml of acetyl chloride is added to a mixture of 0.98 g of 1-(5-amino-2-pyridyl)-2-[2-(dimethylamino)benzylthio]imidazole, 1 ml of triethylamine and 30 ml of methylene chloride under ice-cooling. The mixture is stirred at the same temperature for 2 hours, washed with water and a saturated aqueous sodium bicarbonate solution, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=30:1), and crystallized with isopropyl ether. The crystals are collected by filtration, whereby 0.82 g of 1-(5-acetylamino-2-pyridyl)-2-[2-(dimethylamino)benzylthio]imidazole is obtained.

Workup

  1. temperaturecooling
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium bicarbonate solution, dried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=30:1)
  7. customcrystallized with isopropyl ether
  8. filtrationThe crystals are collected by filtration

Sources & evidence

ORD record
ord-67a7d951c0a24835a8e3dba520e4eaa9
Source dataset
uspto-grants-1991_03
Patent number
US05002945

Reaction notes

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