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Triethylamine → 4-(2,4-Dimethoxyphenyl)pyridine-2,6-dicarboxylic Acid

HRID 5553
Notes
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Reaction equation

HRID 5553 reaction equation
BrCC1C=C(CBr)C=C(CBr)C=1.CCN(CC)CC.C[O:21][C:22]([C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[C:34](S(Cl)(=O)=O)[C:33]([O:40][CH3:41])=[CH:32][C:31]=2[O:42][CH3:43])[CH:27]=[C:26]([C:44]([O:46]C)=[O:45])[N:25]=1)=[O:23].C(NCCO)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl.CO.C(Cl)(Cl)Cl.O>[CH3:43][O:42][C:31]1[CH:32]=[C:33]([O:40][CH3:41])[CH:34]=[CH:35][C:30]=1[C:28]1[CH:27]=[C:26]([C:44]([OH:46])=[O:45])[N:25]=[C:24]([C:22]([OH:23])=[O:21])[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5302581,3,5-Tris(bromomethyl)benzene2×HCID 31256082-((Triphenylmethyl)amino)ethanolHCID 150019164-(5-Chlorosulfonyl-2,4-dimethoxyphenyl)-2,6-pyridine dicarboxylic acid dimethyl ester

Product 1

HCID 150019144-(2,4-Dimethoxyphenyl)pyridine-2,6-dicarboxylic Acid

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

To a suspension of 0.5 g (0.0008 mole) of the amine-hydrochloride 8 in 20 ml of CH2Cl2 was added all at once 1.4 ml (0.01 mole) of Et3N. The mixture was then cooled to 5°-10° C. and 1.4 g (0.0032 mole) of the sulfonyl chloride 39 in 20 ml of CH2Cl2 was slowly added in a dropwise fashion. The reaction was then allowed to stir at room temperature for 30 minutes after which a TLC was taken. Little of the sulfonyl chloride 9 had reacted by TLC so an additional 100 mg of the amine 8 was added and stirring continued overnight. The mixture was then poured into water and extracted with CH2Cl2. The extract was washed with water, dried (Na2SO4) and the solvent removed yielding crude 43. After column chromatography with SiO2 /5%MeOH/CHCl3, 1.55 g (93%) of the desired tetraamide 43 was obtained.

Workup

  1. temperatureThe mixture was then cooled to 5°-10° C.
  2. additionwas added
  3. stirringstirring continued overnight
  4. extractionextracted with CH2Cl2
  5. washThe extract was washed with water
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed
  8. customyielding crude 43

Sources & evidence

ORD record
ord-1c4af60950e34e5ba3caea2d9484da0b
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05245038

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes