Tetrafluoro-m-phenylenediamine dihydrochloride → 5-difluoromethoxy-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]-4,6-dimethyl-1H-benzimidazole

HRID 1789040Notes

Reaction equation

HRID 1789040 reaction equation
[F:1][CH:2]([F:16])[O:3][C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[NH:8][C:9]([SH:11])=[N:10][C:6]=2[C:5]=1[CH3:15].Cl.Cl[CH2:19][C:20]1[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[CH:23]=[CH:22][N:21]=1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CC(O)C>[F:16][CH:2]([F:1])[O:3][C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[NH:8][C:9]([S:11][CH2:19][C:20]3[C:25]([CH3:26])=[C:24]([O:27][CH3:28])[CH:23]=[CH:22][N:21]=3)=[N:10][C:6]=2[C:5]=1[CH3:15]

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 115139822-(Chloromethyl)-4-methoxy-3-methylpyridine--hydrogen chloride (1/1)HCID 178422367HCID 178422367, compound

Product 1

HCID 201895435-difluoromethoxy-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]-4,6-dimethyl-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.0 g of 5-difluoromethoxy-4,6-dimethyl-1H-benzimidazole-2-thiol and 1.72 g of 2-chloromethyl-4-methoxy-3-methylpyridine hydrochloride are heated in 30 ml of 2-propanol for 4 h to the boil. This gives 3.6 g of the dihydrochloride of the title compound. This is dissolved in water and concentrated hydrochloric acid, the solution is clarified with activated charcoal, the product is precipitated with dilute sodium hydroxide solution and the precipitate is recrystallised from butanol. This gives 2.6 g (85%) of the title compound (m.p. 190°-191° C.).

Sources & evidence

ORD record
ord-c5373432472a4323af3eae21f7fcb069
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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