3-Chloro-2,4-pentanedione → HCID 178467552, compound

HRID 1715235Notes

Reaction equation

HRID 1715235 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]([NH2:9])=[S:8])=[N:2]1.Cl[CH:11]([C:15](=O)[CH3:16])[C:12](=[O:14])[CH3:13]>C(O)C>[CH3:16][C:15]1[N:9]=[C:7]([NH:6][C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)[S:8][C:11]=1[C:12](=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 743283-Chloro-2,4-pentanedioneHCID 178514162HCID 178514162, compound

Product 1

HCID 178467552HCID 178467552, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-1H-pyrazol-3-ylthiourea (5 g, 0.0352 mol) in absolute ethanol (50 ml) is added 3-chloro-2,4-pentanedione (4.78 g, 0.0352 mol) and the mixture is refluxed for 20 h under nitrogen. The reaction mixture is cooled down to rt and the resulting precipitate is filtered, washed with ethanol (25 ml) and dried under suction to afford the desired product as hydrochloride salt. It is neutralized with 10% solution of sodium bicarbonate, filtered and dried to afford 1-[4-Methyl-2-(1H-pyrazol-3-ylamino)-1,3-thiazol-5-yl]ethanone as pale brown solid (5 g, 64%). 1H NMR (CD3OD, 300 MHz): δ 2.49 (s, 3H), 2.61 (s, 3H), 6.14 (br s, 1H), 7.62 (br s, 1H). HPLC (Method B), Rt: 4.31 min (purity: 98.07%). TLC—Chloroform/methanol (8/2): Rf 0.4. Mp: 224-227° C.

Workup

  1. temperaturethe mixture is refluxed for 20 h under nitrogen
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with ethanol (25 ml)
  4. customdried under suction

Sources & evidence

ORD record
ord-a9e4b744b68041c3b43dcc1c5dfec8ab
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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