Sodium Hydroxide → 4-Difluoromethoxy-5,6-dimethoxy-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]-1H-benzimidazole

HRID 1789041Notes

Reaction equation

HRID 1789041 reaction equation
[F:1][CH:2]([F:18])[O:3][C:4]1[C:12]2[N:11]=[C:10]([SH:13])[NH:9][C:8]=2[CH:7]=[C:6]([O:14][CH3:15])[C:5]=1[O:16][CH3:17].Cl.Cl[CH2:21][C:22]1[C:27]([CH3:28])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][N:23]=1.[OH-].[Na+]>O.C(O)C>[F:18][CH:2]([F:1])[O:3][C:4]1[C:12]2[N:11]=[C:10]([S:13][CH2:21][C:22]3[C:27]([CH3:28])=[C:26]([O:29][CH3:30])[CH:25]=[CH:24][N:23]=3)[NH:9][C:8]=2[CH:7]=[C:6]([O:14][CH3:15])[C:5]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 115139822-(Chloromethyl)-4-methoxy-3-methylpyridine--hydrogen chloride (1/1)HCID 178486921HCID 178486921, compound

Product 1

HCID 201896014-Difluoromethoxy-5,6-dimethoxy-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]-1H-benzimidazoleYield 87.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.0 g of 4-difluoromethoxy-5,6-dimethoxy-1H-benzimidazole-2-thiol, 0.75 g of 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride, 0.3 g of sodium hydroxide, 2 ml of water and 10 ml of ethanol are stirred for 2.5 h at 60° C. The mixture is poured onto 100 ml of water and cooled in an ice bath. This gives 1.3 g (87%) of the title compound (m.p. 177°-179° C., from diisopropyl ether).

Workup

  1. temperaturecooled in an ice bath

Sources & evidence

ORD record
ord-6a486ee456c447caa9d39a0cf9c900b2
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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