Hydrochloric Acid → 2-[[(2-Aminoethyl)dithio]methyl]-3,5-dimethyl-1-[5-(trifluoromethyl)-2-benzimidazolyl]pyridinium chloride

HRID 35484Notes

Reaction equation

HRID 35484 reaction equation
CC1C(CS([C:12]2[NH:13][C:14]3[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=O)=NC=C(C)C=1.[NH2:25][CH2:26][CH2:27][SH:28].[ClH:29]>O1CCCC1>[Cl-:29].[NH2:25][CH2:26][CH2:27][S:28][S:28][CH2:27][C:26]1[C:17]([CH3:15])=[CH:18][C:19]([CH3:21])=[CH:20][N+:25]=1[C:12]1[NH:13][C:14]2[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6058CysteamineHCID 544464522-[[(3,5-Dimethyl-2-pyridyl)methyl]sulphinyl]-5-(trifluoromethyl)benzimidazole

Product 1

HCID 212958812-[[(2-Aminoethyl)dithio]methyl]-3,5-dimethyl-1-[5-(trifluoromethyl)-2-benzimidazolyl]pyridinium chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.53 g of 2-[[(3,5-dimethyl-2-pyridyl)methyl]sulphinyl]-5 -(trifluoromethyl)benzimidazole are dissolved in 50 ml of tetrahydrofuran and treated with 0.77 g of cysteamine. 40 ml of 3N hydrochloric acid are added thereto at an internal temperature of 40°. The mixture is stirred at 40° overnight and subseguently evaporated in vacuo. The residue is crystallized from tert.butyl methyl ether/ether. There is obtained 2-[[(2-aminoethyl)dithio]methyl]-3,5-dimethyl-1 -[5-(trifluoromethyl)-2-benzimidazolyl]pyridinium chloride of melting point 115°-120°.

Workup

  1. customat an internal temperature of 40°
  2. customsubseguently evaporated in vacuo
  3. customThe residue is crystallized from tert.butyl methyl ether/ether

Sources & evidence

ORD record
ord-95f22f69963446b3a4ee940056743b5e
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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