Hydrogen Sulfide → Thiobenzamide, 2-bromo-

HRID 1080727Notes

Reaction equation

HRID 1080727 reaction equation
[SH2:1].[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].C(N(CC)CC)C>N1C=CC=CC=1>[Br:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]([NH2:6])=[S:1]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 162722-Bromobenzonitrile

Product 1

HCID 2734818Thiobenzamide, 2-bromo-Yield 68%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Gaseous hydrogen sulfide was bubbled into a stirred solution of 1.82 g (10.0 mmol) of 2-bromobenzonitrile, 13 mL of triethylamine and 10 mL of pyridine. After 4 hours, the reaction mixture was poured into 200 mL of ice-water mixture. The resultant oil slowly crystallized. The precipitate was removed by filtration, washed with water (3×) and dissolved in methylene chloride. The organic layer was separated, dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum to give 1.46 g (6.76 mmol, 68%) of the product. 1H NMR (200 MHz, CDCl3): 7.24 (m, 4H), 7.52 (dt, 1H), 8.59 (dd, 1H).

Workup

  1. customThe resultant oil slowly crystallized
  2. customThe precipitate was removed by filtration
  3. washwashed with water (3×)
  4. dissolutiondissolved in methylene chloride
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-9156b7715a5f483b8cf16e9805e80264
Source dataset
uspto-grants-1996_12
Patent number
US05583130

Reaction notes

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