2-Phenylethanethiol → HCID 178511849, compound

HRID 2289617Notes

Reaction equation

HRID 2289617 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: 1H NMR (DMSO-d6) δ12.85 (br s, 1H, SH), 7.5-7.2 (m, 4H, 4×ArH) ppm; IR (KBr) ν 2259, 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-b72da74f33504cca96e6efd0f4f52196
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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