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2,4,6-Trimethylaniline → HCID 66717386, compound

HRID 2105279
Notes
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Reaction equation

HRID 2105279 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].C(N(CC)CC)C.[C:18]1([S:24]([NH:27][C:28]2[CH:32]=[CH:31][S:30][C:29]=2[C:33](Cl)=[O:34])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCCCCC.C(OCC)(=O)C>ClCCl>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH:4][C:33]([C:29]1[S:30][CH:31]=[CH:32][C:28]=1[NH:27][S:24]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:25])=[O:26])=[O:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 69132,4,6-TrimethylanilineHCID 8471TriethylamineHCID 21226206Ethyl acetate hexane2×HCID 858183133-Benzenesulfonylaminothiophene-2-carboxylic acid chloride

Product 1

HCID 66717386HCID 66717386, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 2,4,6-trimethylaniline (70 mg, 0.518 mmol) in dichloromethane (0.20 mL) and triethylamine (72□ L, 0.52 mmol) was added 3-benzenesulfonylamino-thiophene-2-carboxylic acid chloride (134 mg, 0.444 mmol). The resulting mixture was allowed to stir overnight at room temperature under a nitrogen atmosphere. The reaction mixture was applied directly to silica gel, (9:1 hexane/ethyl acetate, gradient to 4:1 hexane ethyl acetate). The compound was then precipitated from hexanes and dichloromethane to give 3-benzenesulfonylamino-thiophene-2-carboxylic acid (2,4,6-trimethylphenyl) amide as a white solid (0.028 g, 16%).

Workup

  1. customThe compound was then precipitated from hexanes and dichloromethane

Sources & evidence

ORD record
ord-bbb7d474e3a540a0a7ecd12f69a1ea32
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07579340B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes