Triethylamine → 5-Bromo-2-fluorobenzene-1-carbothioamide

HRID 521918Notes

Reaction equation

HRID 521918 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[NH4+]=[S:12].C(N(CC)CC)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([C:7](=[S:12])[NH2:8])[CH:9]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 826479225-Bromo-2-fluorobenzene-1-carbothioamideYield 97.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

5-bromo-2-fluoro-benzonitrile (12.4 mmol, 2470 mg) in pyridine (6.5 mL) was treated with ammonium sulfide (40 mass % in water, 1.1 equiv., 13.6 mmol, 2.32 mL) and triethylamine (1.1 equiv., 13.6 mmol, 1.90 mL). The reaction mixture was heated at 50° C. for 3 hours, then cooled to room temperature. The reaction mixture was partitioned between EtOAc and water. The organic later was washed with water (3×), and brine (3×), dried with MgSO4, then concentrated. The residue was purified on silica eluted with 0 to 50% EtOAc in Heptane to provide 5-bromo-2-fluoro-benzenecarbothioamide (2.84 g, 94% yield).

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. washThe organic later was washed with water (3×), and brine (3×)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on silica
  7. washeluted with 0 to 50% EtOAc in Heptane

Sources & evidence

ORD record
ord-a1b5d8e246564b96b2c077f3325fefd1
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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