p-Toluenesulfonic acid monohydrate → HCID 72359933, compound

HRID 2103886Notes

Reaction equation

HRID 2103886 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([C:15]([CH3:17])=O)[C:13]=2[OH:14])=[CH:5][CH:4]=1.[NH:20]([C:22]([C:24]1[S:28][C:27]([C:29]([O:31][CH3:32])=[O:30])=[CH:26][CH:25]=1)=[O:23])[NH2:21].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([C:15](=[N:21][NH:20][C:22]([C:24]3[S:28][C:27]([C:29]([O:31][CH3:32])=[O:30])=[CH:26][CH:25]=3)=[O:23])[CH3:17])[C:13]=2[OH:14])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 148719615-Methoxycarbonyl-2-thiophenecarboxylic acid hydrazideHCID 602067891-{4-Hydroxy-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}ethan-1-one

Product 1

HCID 72359933HCID 72359933, compoundYield 72.6%

Procedure

From 2-(4-trifluoromethylphenyl)-3-hydroxy-4-methylcarbonylthiophene (57.3 mg, 0.2 mmol), methyl 5-hydrazinocarbonyl-2-thiophenecarboxylate (40.0 mg, 0.2 mmol) and tosylic acid monohydrate (11.4 mg, 0.06 mmol), 68.0 mg of the desired product was obtained in the same manner as in Synthetic Example 65 as a pale yellow solid (yield 73%).

Sources & evidence

ORD record
ord-fefd2e506e014c9f93043263586a5905
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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