2-Phenylethanethiol → HCID 178511849, compound

HRID 1489008Notes

Reaction equation

HRID 1489008 reaction equation
Br[C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1.C(S)CC1C=CC=CC=1>CO>[SH:4][C:5]1[N:9]([C:2]#[N:3])[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 781262-PhenylethanethiolHCID 10198942HCID 10198942, compound

Product 1

HCID 178511849HCID 178511849, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 500 mg of 3-bromo-1,2,4-thiadiazolo [4,5-a]benzimidazole in 50 mL methanol was added 790 μL of phenethyl mercaptan. The solid rapidly dissolves. After completion of the reaction, the solvent was evaporated and the residue purified by chromatography to give 296 mg of 2-mercapto-1-benzimidazolecarbonitrile:=H NMR (DMSO-d6) δ12.85 (br s, 1H, SH), 7.5-7.2 (m, 4H, 4×ArH) ppm; IR (KBr) ν2259, 1509, 1459, 1303, 1189, 752 cm-1 ; MS m/z 175 (M+), 150 (M+ -CN).

Workup

  1. dissolutionThe solid rapidly dissolves
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-1d2666ea93eb4e549b28afd2bd69fa4b
Source dataset
uspto-grants-1997_10
Patent number
US05677302

Reaction notes

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