Sodium Hydroxide → 5,6-Dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole

HRID 1709772Notes

Reaction equation

HRID 1709772 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.Cl.Cl[CH2:15][C:16]1[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][N:17]=1.[OH-].[Na+]>O>[Cl:12][C:11]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]=[C:7]([S:9][CH2:15][C:16]3[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][N:17]=3)[NH:6][C:5]=2[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 115139822-(Chloromethyl)-4-methoxy-3-methylpyridine--hydrogen chloride (1/1)HCID 178527798HCID 178527798, compound

Product 1

HCID 230365205,6-Dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 13 g of 5,6-dichloro-2-benzimidazolethiol in 360 ml of alcohol was treated with 13 g of 2-chloromethyl-4-methoxy 3-methylpyridine hydrochloride. A solution of 4 g of sodium hydroxide in 170 ml of water was added dropwise thereto while cooling with ice. The mixture was left to boil at reflux overnight and then concentrated to about 1/3 of its volume in a vacuum. After the addition of 600 ml of water the crystals were filtered off and thereupon washed thoroughly with water and then with ether. There was obtained 5,6-dichloro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole of melting point 254°-256°.

Workup

  1. temperaturewhile cooling with ice
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. concentrationconcentrated to about 1/3 of its volume in a vacuum
  5. additionAfter the addition of 600 ml of water the crystals
  6. filtrationwere filtered off
  7. washwashed thoroughly with water

Sources & evidence

ORD record
ord-9bc976dbf06f4df69929fd04985c2d27
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

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