p-Toluenesulfonic acid monohydrate → methyl 5-[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylate

HRID 1881632Notes

Reaction equation

HRID 1881632 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=O)[CH3:16])[C:10]=2[OH:18])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:19]([C:21]([C:23]1[S:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:24]=1)=[O:22])[NH2:20].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([CH3:14])[N:12]=[C:11]([C:15](=[N:20][NH:19][C:21]([C:23]3[S:27][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:24]=3)=[O:22])[CH3:16])[C:10]=2[OH:18])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 148719615-Methoxycarbonyl-2-thiophenecarboxylic acid hydrazideHCID 602067801-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone

Product 1

HCID 72359955methyl 5-[(2-{1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethylidene}hydrazino)carbonyl]-2-thiophenecarboxylateYield 96%

Procedure

From 1-[5-(3,4-dichlorophenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (200 mg, 0.70 mmol) synthesized in Synthetic Example 1, methyl 5-hydrazinocarbonyl-2-thiophenecarboxylate (0.70 mmol, 140.4 mg) of Reference Synthetic Example 39 and tosylic acid monohydrate (36.2 mg, 0.21 mmol), 314.1 mg of the desired product was obtained in the same manner as in Synthetic Example 58 as a yellow solid (yield 96%).

Sources & evidence

ORD record
ord-c0bd846de1654e1c8f92070e8cd882f3
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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