Hydrogen Sulfide → HCID 24700409, compound

HRID 1716848Notes

Reaction equation

HRID 1716848 reaction equation
[N:1]1([CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(N(CC)CC)C.[SH2:26]>N1C=CC=CC=1.O>[N:1]1([CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15](=[S:26])[NH2:16])=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 8635584-(1H-1,3-benzodiazol-1-ylmethyl)benzonitrile

Product 1

HCID 24700409HCID 24700409, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A stirred solution of 4-(1H-benzimidazol-1-ylmethyl)benzonitrile (0.50 g, 2.14 mmol) and triethylamine (Et3N) (0.24 g, 2.37 mmol) in pyridine (2 mL), was bubbled through with H2S (g) at room temperature for 2 h. The reaction mixture was diluted with water and filtered. The filtercake was washed with cold water and dried under vacuum to afford the title compound in 87% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 5.54 (s, 2H), 7.16-7.22 (m, 2H), 7.30 (d, J=8.8 Hz, 2H), 7.45-7.52 (m, 1H), 7.62-7.68 (m, 1H), 7.79 (d, J=8.8 Hz, 2H), 9.30 (bs, 1H), 9.80 (bs, 1H). LCMS (ESI+) 268 (MH+).

Workup

  1. filtrationfiltered
  2. washThe filtercake was washed with cold water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-aa313dacbeb44c12ad85adf35fa0bfc4
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

Loading…