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

HRID 1029355

Reaction equation

HRID 1029355 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.CS[C:27]1[S:28][C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[N+:31]=1[CH3:32].C(N(CC)CC)C>CO>[CH3:32][N:31]1[C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[S:28](=[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])[CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41464Benzothiazolium, 3-methyl-2-(methylthio)-, 4-methylbenzenesulfonate (1:1)HCID 703351H-Pyrazol-5-ol, 3-methyl-1-phenyl-

Product 1

HCID 867456114-[-3-Methylbenzothiazolinylidene]-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 3.68 g (0.01 mol) 2-methylthio-3-methylbenzothiazolium tosylate in 25 ml methanol. Triethylamine (1.01 g, 0.01 mol) was added. The mixture was stirred for one hour, then filtered and washed with methanol. After drying the yield was 2.46 g (78%), mp 159°-162° C., λmax=375 (ε=25,000).

Workup

  1. filtrationfiltered
  2. washwashed with methanol
  3. customAfter drying the yield was 2.46 g (78%), mp 159°-162° C., λmax=375 (ε=25,000)

Sources & evidence

ORD record
ord-6cbb14defca149e0998b6ab85d6dad14
Source dataset
uspto-grants-1992_04
Patent number
US05102781

Linked notes

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