Sodium Hydroxide → HCID 19024498, compound

HRID 1709758Notes

Reaction equation

HRID 1709758 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.Cl.Cl[CH2:14][C:15]1[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[CH:18]=[CH:17][N:16]=1.[OH-].[Na+]>O>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[CH:18]=[CH:17][N:16]=3)[NH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 34348856-fluoro-1H-benzimidazole-2-thiolHCID 115139822-(Chloromethyl)-4-methoxy-3-methylpyridine--hydrogen chloride (1/1)

Product 1

HCID 19024498HCID 19024498, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.6 g of 5-fluoro-2-benzimidazolethiol were suspended in 570 ml of alcohol and treated with 13.1 g of 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride. A solution of 5 g of sodium hydroxide in 130 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 the volume in a vacuum. After the addition of 500 ml of water the resulting crystals were filtered off and washed thoroughly firstly with water and then with ether. There was obtained 5-fluoro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]benzimidazole of melting point 128°.

Workup

  1. temperaturewhile cooling with ice
  2. waitthe mixture was left
  3. temperatureat reflux overnight
  4. concentrationconcentrated to about 1/3 of the volume in a vacuum
  5. additionAfter the addition of 500 ml of water the resulting crystals
  6. filtrationwere filtered off
  7. washwashed thoroughly firstly with water

Sources & evidence

ORD record
ord-8dafc7d0ea70437d80b012f503170dae
Source dataset
uspto-grants-1990_08
Patent number
US04950677

Reaction notes

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