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

HRID 1881620Notes

Reaction equation

HRID 1881620 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-1a3a16e89f8f408991d11de5cc8943ec
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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