p-Toluenesulfonic acid monohydrate → Methyl 2-nitro-4-[(2-{1-[5-(4-trifluoromethylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino) carbonyl]benzoate

HRID 2103888Notes

Reaction equation

HRID 2103888 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[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[C:26]([N+:34]([O-:36])=[O:35])[CH:25]=1)=[O:23])[NH2:21].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>>[N+:34]([C:26]1[CH:25]=[C:24]([C:22]([NH:20][N:21]=[C:15]([C:12]2[C:13]([OH:14])=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:4][CH:5]=3)[S:10][CH:11]=2)[CH3:17])=[O:23])[CH:33]=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29])([O-:36])=[O:35]

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 602067891-{4-Hydroxy-5-[4-(trifluoromethyl)phenyl]thiophen-3-yl}ethan-1-oneHCID 669863564-Methoxycarbonyl-3-nitrobenzhydrazide

Product 1

HCID 72359929Methyl 2-nitro-4-[(2-{1-[5-(4-trifluoromethylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino) carbonyl]benzoateYield 80.5%

Procedure

From 2-(4-trifluoromethylphenyl)-3-hydroxy-4-methylcarbonylthiophene (57.3 mg, 0.2 mmol), methyl 4-hydrazinocarbonyl-2-nitrobenzoate (47.8 mg, 0.2 mmol) and tosylic acid monohydrate (11.4 mg, 0.06 mmol), 81.7 mg of the desired product was obtained in the same manner as in Synthetic Example 65 as a pale yellow solid (yield 81%).

Sources & evidence

ORD record
ord-680f3a1da70f41de827a3296c4758a98
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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