Hydrogen Sulfide → HCID 21083989, compound

HRID 347935Notes

Reaction equation

HRID 347935 reaction equation
[SH2:1].[O:2]=[C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]2[S:15][C:16]([C:24]#[N:25])=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:5]=[CH:4]1>N1C=CC=CC=1.C(N(CC)CC)C>[O:2]=[C:3]1[N:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:7]2[S:15][C:16]([C:24](=[S:1])[NH2:25])=[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:5]=[CH:4]1

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 9858633HCID 9858633, compound

Product 1

HCID 21083989HCID 21083989, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

Hydrogen sulphide was bubbled through a solution of the compound of Example 77 (539 mg, 1.64 mmol) in pyridine (1 0 mL) and triethylamine (0.5 mL) for 30 minutes. The reaction was left to stand for 60 h at r.t. and then nitrogen bubbled through the mixture to ensure the solution was purged of H2S. The solution was diluted with DCM and washed with water (×2), 2M HCl(aq) (×2) and brine. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was recrystallised from DCM-hexane to give the title compound as a solid (327 mg, 40%). δH (DMSO-d6) 9.70 (1H, s), 7.70–7.47 (9H, m), 7.45 (2H, m), 7.38 (1H, d J 9.6 Hz), 6.52 (1H, d, J 9.6 Hz). LCMS (ES+) RT 3.33 minutes, 385 (M+Na)+, 363 (M+H)+.

Workup

  1. waitThe reaction was left
  2. customnitrogen bubbled through the mixture
  3. customwas purged of H2S
  4. additionThe solution was diluted with DCM
  5. washwashed with water (×2), 2M HCl(aq) (×2) and brine
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was recrystallised from DCM-hexane

Sources & evidence

ORD record
ord-0f02878d866b4fcab944300b6652a03c
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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