Hydrogen Sulfide → 1H-Indole-5-carbothioamide

HRID 2416200Notes

Reaction equation

HRID 2416200 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[SH2:12]>N1C=CC=CC=1>[NH:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1](=[S:12])[NH2:2])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 27513Indole-5-carbonitrile

Product 1

HCID 179958021H-Indole-5-carbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-cyanoindole (Aldrich) (2.84 g, 20.0 mmol) in 20 mL of pyridine and 8.35 mL of TEA was purged with H2S gas for 1.5 h. Solvents were removed under vacuum. The residue was dissolved in 100 mL of EtOAc, washed with H2O, 0.3 N HCl (aq.), and H2O. The EtOAc layer was separated, dried (Na2SO4), and concentrated to yield the corresponding 5-indole-thiocarboxamide that was used directly in the next step. A solution of 5-indole-thiocarboxamide (150 mg, 0.85 mmol) and 3-(2-bromoacetyl)hydroquinolin-2-one (Example 27, 120 mg, 0.45 mmol) in 50 mL of MeOH was heated at reflux for 4 h. The mixture was then concentrated. The residue was treated with CH2Cl2 and the precipitates were collected by filtration to provide the title compound as a pale orange solid. MS m/z: 344 (M+1). Anal. Calc'd for C20H13N3OS.H2O.0.8HBr: C, 56.37; H, 3.74; N, 9.86; O, 7.51; S, 7.52. Found: C, 56.64; H, 3.80; N, 9.64; O, 7.30; S, 7.44.

Workup

  1. customSolvents were removed under vacuum
  2. dissolutionThe residue was dissolved in 100 mL of EtOAc
  3. washwashed with H2O, 0.3 N HCl (aq.), and H2O
  4. customThe EtOAc layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-02a7bf272bfb43f6841fcfa63bcb8794
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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