Hydrogen Sulfide → HCID 19063817, compound

HRID 482251Notes

Reaction equation

HRID 482251 reaction equation
[SH2:1].[CH3:2][C:3]1[CH:4]=[C:5]([O:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)(=[O:22])=[O:21])[CH:6]=[C:7]([O:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][N:16]=[N:15][CH:14]=2)[CH:8]=1.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:2][C:3]1[CH:4]=[C:5]([O:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29](=[S:1])[NH2:30])[CH:24]=2)(=[O:22])=[O:21])[CH:6]=[C:7]([O:9][CH2:10][CH2:11][NH:12][C:13]2[CH:18]=[CH:17][N:16]=[N:15][CH:14]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 19063819HCID 19063819, compound

Product 1

HCID 19063817HCID 19063817, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrogen sulfide was passed into a solution of 1.5 g (3.7 mmol) 3-cyanobenzenesulfonic acid-3-methyl-5-[2-(pyridazin-4-ylamino)-ethoxy]-phenyl ester (example 9) and 2.0 ml triethylamine in 20 ml pyridine until saturation (ca. 30 min). After 2 h at room temperature the solvent was removed in a vacuum, the residue was admixed with water, extracted with ethyl acetate, the solvent was removed in a vacuum, the residue was taken up in methanol and filtered over silica gel (dichloromethane: methanol=98:2). The solvent was removed in a vacuum and the title compound was obtained in a 87% yield as yellow crystals of Fp 76°-78° C.

Workup

  1. customAfter 2 h at room temperature the solvent was removed in a vacuum
  2. extractionextracted with ethyl acetate
  3. customthe solvent was removed in a vacuum
  4. filtrationfiltered over silica gel (dichloromethane: methanol=98:2)
  5. customThe solvent was removed in a vacuum

Sources & evidence

ORD record
ord-2502fb819e3e422787bf435dd30ecc8d
Source dataset
uspto-grants-1998_08
Patent number
US05795892

Reaction notes

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