p-Toluenesulfonic acid monohydrate → HCID 72359967, compound

HRID 1881657Notes

Reaction equation

HRID 1881657 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12](=C=O)[CH:13]=[C:14]([CH3:17])[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Si]([O:27][CH2:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([NH:35][NH2:36])=[O:34])=[CH:31][C:30]=1[N+:39]([O-:41])=[O:40])(C(C)(C)C)(C)C.O.[C:43]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:17](=[N:36][NH:35][C:33](=[O:34])[C:32]3[CH:37]=[CH:38][C:29]([CH2:28][OH:27])=[C:30]([N+:39]([O-:41])=[O:40])[CH:31]=3)[CH3:43])[C:15]=2[OH:16])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67050227HCID 67050227, compoundHCID 86604760HCID 86604760, compound

Product 1

HCID 72359967HCID 72359967, compoundYield 248.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2-(4-tert-butylphenyl)-3-hydroxy-4-methyl-carbonylthiophene (27.8 mg, 0.10 mmol), 4-(tert-butyl-dimethylsilanyloxymethyl)-3-nitrobenzoic acid hydrazide (34.9 mg, 0.11 mmol) and p-toluenesulfonic acid monohydrate (5.7 mg, 0.03 mmol) in isopropanol (1.0 mL) was stirred at 95° C. for 7 hours. The precipitated solid was collected by filtration and dried by means of a vacuum pump to give the desired product as yellow solid (34.8 mg, yield 73%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customdried by means of a vacuum pump

Sources & evidence

ORD record
ord-0e72bd022eb740e0888b220bd7206e86
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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