Benzenemethanethiol, alpha,alpha-diphenyl- → HCID 20079589, compound

HRID 1654164Notes

Reaction equation

HRID 1654164 reaction equation
[C:1]([SH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].CO.Cl[CH2:27][CH2:28][N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[CH:30]1>C(O)C>[C:1]([S:20][CH2:27][CH2:28][N:29]1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[N:31]=[CH:30]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 5831471-(2-Chloroethyl)-1H-benzimidazoleHCID 23694274Sodium methanolate methanol

Product 1

HCID 20079589HCID 20079589, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trityl mercaptan (9.7 g, 35 mmol) in ethanol (90 ml) was added, at 0° C., a sodium methoxide-methanol solution (28%) (7.1 ml). To the reaction mixture was added 1-(2-chloroethyl)benzimidazole (6.32 g, 35 mmol), which was heated for 2 hours under reflux. Insoluble substances were filtered off, and the filtrate was concentrated under reduced pressure. The concentrate was subjected to a silica gel column chromatography (3.0×40 cm: ethyl acetate:hexane=1:1→2:1) to give 1-(2-tritylthioethyl)benzimidazole (5.6 g, 38%).

Workup

  1. temperaturewas heated for 2 hours
  2. temperatureunder reflux
  3. filtrationInsoluble substances were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5bcd786438974f66b3d6cf726cbc6b42
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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