Tetrafluoro-m-phenylenediamine dihydrochloride → 2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole dihydrochloride

HRID 1081676Notes

Reaction equation

HRID 1081676 reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:13].Cl.[SH:15][C:16]1[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=1.Cl.[Cl:26][CH2:27][C:28]1[C:33]([CH3:34])=[C:32]([S:35][CH2:36][C:37]2[O:38][CH:39]=[CH:40][CH:41]=2)[CH:31]=[CH:30][N:29]=1>C(O)(C)C>[ClH:26].[ClH:13].[O:38]1[CH:39]=[CH:40][CH:41]=[C:37]1[CH2:36][S:35][C:32]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:27][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[C:33]=1[CH3:34]

Participants

5

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 224607712-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochlorideHCID 178527775HCID 178527775, compound

Product 1

HCID 233630132-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole dihydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The compound of Example 1 can also be prepared via the corresponding dihydrochloride, by refluxing 2-mercapto-1H-benzimidazole (1.5 g/10 mmol) in 30 ml of isopropanol with 2-chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride (10 mmol) for 5 h, cooling, removing the precipitated solid by filtration and recrystallizing this from isopropanol/water. This gives the title compound (yield 90%) as a colorless solid of m.p. 208° C. (decomp.).

Workup

  1. temperaturecooling
  2. customremoving the precipitated solid
  3. filtrationby filtration
  4. customrecrystallizing this from isopropanol/water

Sources & evidence

ORD record
ord-cb48ea72063f433fa68bfddd682c1610
Source dataset
uspto-grants-1996_12
Patent number
US05587389

Reaction notes

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