Triethylamine → 4-[3-Ethylbenzothiazolinylidene]-3-methyl-1-phenylpyrazolin-5-one

HRID 1029363Notes

Reaction equation

HRID 1029363 reaction equation
[CH3:1][C:2]1[NH:3][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5](=[O:7])[CH:6]=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C(S[C:28]1[S:29][C:30]2[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=2[N+:32]=1[CH2:33][CH3:34])C.C(N(CC)CC)C>CO>[CH2:33]([N:32]1[C:31]2[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=2[S:29](=[C:6]2[C:5](=[O:7])[N:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:3][CH:2]2[CH3:1])[CH2:28]1)[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703351H-Pyrazol-5-ol, 3-methyl-1-phenyl-HCID 140905473-Ethyl-2-(ethylsulfanyl)-1,3-benzothiazol-3-ium 4-methylbenzene-1-sulfonate

Product 1

HCID 867456164-[3-Ethylbenzothiazolinylidene]-3-methyl-1-phenylpyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Methyl-1-phenylpyrazolin-5-one (1.74 g, 0.01 mol) was mixed with a methanol solution of 2-ethylthio-3-ethylbenzothiazolium tosylate. Triethylamine (1.01 g, 0.01 mol) was added. The mixture was stirred for 10 minutes, then concentrated and treated with isopropanol. The mixture was heated to dissolve the product, then water was added to cloud, and the mixture cooled to give crystals: 3.22 g (48%), mp 144°-147.5° C., λmax=379 (ε=25,000).

Workup

  1. concentrationconcentrated
  2. additiontreated with isopropanol
  3. temperatureThe mixture was heated
  4. dissolutionto dissolve the product
  5. additionwater was added to cloud
  6. temperaturethe mixture cooled
  7. customto give crystals

Sources & evidence

ORD record
ord-b931c63ecf554f069f4279a9ac934fab
Source dataset
uspto-grants-1992_04
Patent number
US05102781

Reaction notes

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