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 2103900Notes

Reaction equation

HRID 2103900 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-473c59df966e45f69b0063dbf7c6a5f5
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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