Triethylamine → 4-[5-Methoxy-3-methylbenzothiazolinylidene]-3-methyl-1-phenylpyrazolin-5-on

HRID 1029358

Reaction equation

HRID 1029358 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.[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[S:34][C:33](SC)=[N+:32]([CH3:37])[C:31]=2[CH:38]=1.C(N(CC)CC)C>CO>[CH3:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[S:34](=[C:6]3[C:5](=[O:7])[N:4]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[NH:3][CH:2]3[CH3:1])[CH2:33][N:32]([CH3:37])[C:31]=2[CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703351H-Pyrazol-5-ol, 3-methyl-1-phenyl-HCID 867456125-Methoxy-2-methylthio-3-methylbenzothiazolium tosylate

Product 1

HCID 867456134-[5-Methoxy-3-methylbenzothiazolinylidene]-3-methyl-1-phenylpyrazolin-5-on

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Methyl-1-phenylpyrazolin-5-one (1.74 g, 0.01 mol) was mixed with 3.97 g (0.01 mol) 5-methoxy-2-methylthio-3-methylbenzothiazolium tosylate in 25 ml methanol. Triethylamine (1.01 g, 0.01 mol) was added. The mixture was stirred for 3.5 hours, then filtered and washed with methanol. After drying the yield was 276 g (79%), mp 155°-156° C., λmax=386 (ε=25,000).

Workup

  1. filtrationfiltered
  2. washwashed with methanol
  3. customAfter drying the yield was 276 g (79%), mp 155°-156° C., λmax=386 (ε=25,000)

Sources & evidence

ORD record
ord-5ddf10501a9142da9f7d5ad3f0804a4a
Source dataset
uspto-grants-1992_04
Patent number
US05102781

Linked notes

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