Thionyl Chloride → 2-Chloromethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridine

HRID 342640Notes

Reaction equation

HRID 342640 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][CH2:16][CH2:17][N:18]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]2[CH3:26])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:29])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:29][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15][CH2:16][CH2:17][N:18]2[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][N:20]=[C:19]2[CH3:26])[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 538997552-Hydroxymethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridine

Product 1

HCID 544598052-Chloromethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4 g (10 mmol) of 2-hydroxymethyl-3-methyl-4-{4-[2-(2-methyl-5-nitroimidazol-1-yl)ethylthio]butylthio}-pyridine are dissolved in 40 ml of dichloromethane. 1.56 g (13.11 mmol) of thionyl chloride in 5 ml of dichloromethane are added dropwise with ice-cooling. The mixture is stirred at 0C for 2 h. It is then added to 250 ml of ice-water and neutralized with saturated sodium hydrogen carbonate solution. The dichloromethane phase is separated off and the aqueous phase is extracted again with dichloromethane. The combined organic phases are washed with water, dried over magnesium sulfate, filtered and concentrated. The title compound is obtained as a yellow oil which is reacted without further purification. Yield 4.15 g (100% of theory).

Workup

  1. temperaturecooling
  2. customThe dichloromethane phase is separated off
  3. extractionthe aqueous phase is extracted again with dichloromethane
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-22fd99d6b14a45b1a9dde0fde42a0d7b
Source dataset
uspto-grants-1999_01
Patent number
US05859030

Reaction notes

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