Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 3000733, compound

HRID 2229781Notes

Reaction equation

HRID 2229781 reaction equation
[C:1]([CH2:9][C:10]([O:12]CC)=O)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[NH2:15][C:16]([NH2:18])=[S:17].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC1C=CC(C)=CC=1>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[NH:18][C:16](=[S:17])[NH:15][C:10](=[O:12])[CH:9]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 2723790ThioureaHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

Product 1

HCID 3000733HCID 3000733, compound

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

Ethyl isonicotinoylacetate (5 g, 25.89 mmol) and thiourea (5.94 g, 77.64 mmol) were suspended in anhydrous p-xylene (100 ml) with vigorous stirring. To the mixture, pyridinium p-toluenesulfonate (150 mg) was added and refluxed for 12-16 h using a Dean-Stark apparatus with continuous removal of water (0.5 ml). The reaction mixture was cooled and a dark brown solid was filtered. The collected solid was suspended in acetone (25 ml) and filtered. The acetone washed product contain trace of thiourea, which was removed by trituration with hot water (20-30 ml). The title compound was isolated by filtration. MS (m/z): 206.2 C9H7N3OS requir. 205.3. 1H-NMR (DMSO-d6): d 12.65 (bm, 2H, NH and SH), 8.71(m, 2H, pryid.), 7.66(m, 2H, Pyrid.), 6.25 (s, 1H, H-5).

Workup

  1. temperaturerefluxed for 12-16 h
  2. customwith continuous removal of water (0.5 ml)
  3. temperatureThe reaction mixture was cooled
  4. filtrationa dark brown solid was filtered
  5. filtrationfiltered
  6. customwas removed by trituration with hot water (20-30 ml)

Sources & evidence

ORD record
ord-7d4d624ece5c4087a4639244228e6c0b
Source dataset
uspto-grants-2002_07
Patent number
US06420385B1

Reaction notes

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