Pyridine → 2-(1H-Benzimidazol-1-yl)ethane-1-thiol

HRID 1654165Notes

Reaction equation

HRID 1654165 reaction equation
C([S:20][CH2:21][CH2:22][N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[CH:24]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.N1C=CC=CC=1.[N+]([O-])([O-])=O.[Ag+:42]>CO.C(Cl)(Cl)Cl>[Ag:42].[SH:20][CH2:21][CH2:22][N:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[CH:24]1

Participants

7

Reactant 3

HCID 1049PyridineHCID 24470Silver NitrateHCID 20079589HCID 20079589, compound

Product 2

HCID 23954SilverHCID 152944272-(1H-Benzimidazol-1-yl)ethane-1-thiolYield 159.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 1-(2-tritylthioethyl)benzimidazole (7.0 g, 16.6 mmol) in a mixture of methanol (50 ml) and chloroform (80 ml), were added pyridine (1.32 ml, 16.3 mmol) and then silver nitrate (2.9 g, 17.1 mmol). The mixture was stirred for 3 hours at room temperature. Precipitates then separated out were collected and washed with methanol and then with ethyl ether to give silver salt of 1-(2-mercaptoethyl)benzimidazole (4.73 g, 99%). The silver salt (4.73 g, 16.6 mmol) was suspended in dichloromethane (250 ml), which was bubbled with hydrogen sulfide at 0° C. for one hour. Precipitates were filtered off, and the filtrate was concentrated to give 1-(2-mercaptoethyl)benzimidazole (2.35 g, 79%) as colorless powder (2.35 g, 79%).

Workup

  1. customPrecipitates
  2. customthen separated out
  3. customwere collected
  4. washwashed with methanol

Sources & evidence

ORD record
ord-de1ccbea2fa14cc8bad03046c7e74a73
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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