Thionyl Chloride → HCID 10735330, compound

HRID 1957764Notes

Reaction equation

HRID 1957764 reaction equation
O[CH2:2][C:3]([NH:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([NH:17][C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=O)=[C:11]([O:23][CH3:24])[C:10]=1[O:25][CH3:26])=[O:8])([CH3:5])[CH3:4].S(Cl)(Cl)=O>CCOCC>[CH3:26][O:25][C:10]1[C:11]([O:23][CH3:24])=[C:12]([C:15]2[O:20][CH2:19][C:18]([CH3:21])([CH3:22])[N:17]=2)[CH:13]=[CH:14][C:9]=1[C:7]1[O:8][CH2:5][C:3]([CH3:2])([CH3:4])[N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 19068449HCID 19068449, compound

Product 1

HCID 10735330HCID 10735330, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 6.00 g (16.3-mmol) of N,N'-bis(2-hydroxy-1,1-dimethylethyl)-2,3-dimethoxy-1,4-phenylenedicarboxamide, was added 7.0 mL (96.0 mmol) of thionyl chloride. The mixture was stirred at room temperature for 3 hours. Further thereto, 7.0 mL (96.0 mmol) of thionyl chloride was added, and the mixture was stirred at room temperature for one hour. The reaction solution was poured into 50 mL of ether. The supernatant liquid was removed by decantation. Aqueous 10% sodium hydroxide solution was added to the residue to bring the pH to 8. It was extracted with ether, and was dried over anhydrous sodium sulfate. The solvent was removed by distillation, and the residue was purified by silca gel column chromatography (methylene chloride:ethanol=20:1) to obtain 2.52 g (47%) of 2,2'-(2,3-dimethoxy-1,4-phenylene)-bis (4,4-dimethyl-2-oxazoline) in a colorless crystal state.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. customThe supernatant liquid was removed by decantation
  3. additionAqueous 10% sodium hydroxide solution was added to the residue
  4. extractionIt was extracted with ether
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. customthe residue was purified by silca gel column chromatography (methylene chloride:ethanol=20:1)

Sources & evidence

ORD record
ord-16d0cfef401645d7af9378c73ce3ad00
Source dataset
uspto-grants-1998_07
Patent number
US05786486

Reaction notes

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