Dimethylformamide → HCID 22403161, compound

HRID 259754Notes

Reaction equation

HRID 259754 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[Br:11][C:12]1[C:13]([O:24][CH3:25])=[C:14]([C:19]2[NH:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[C:16]([Br:18])[CH:17]=1.C([O-])(=O)C.[Na+]>ClCCCl>[Br:11][C:12]1[C:13]([O:24][CH3:25])=[C:14]([C:19]2[NH:20][C:21]([CH:8]=[O:9])=[CH:22][CH:23]=2)[CH:15]=[C:16]([Br:18])[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 110780591H-Pyrrole, 2-(3,5-dibromo-2-methoxyphenyl)-

Product 1

HCID 22403161HCID 22403161, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Phosphorus oxychloride (0.18 ml, 1.9 mmol) was added to N,N-dimethylformamide (0.15 ml, 1.9 mmol) at 0° C. under argon with constant stirring. The resulting mixture was allowed to warm to room temperature and was then stirred for 1.5 h. 1,2-Dichloroethane (1.5 ml) was added and a solution of 2-(3,5-dibromo-2-methoxyphenyl)-1H-pyrrole (0.30 g, 0.91 mmol) in 1,2-dichloroethane (3 ml) was then added at 0° C. The reaction mixture was stirred at room temperature for 16 h. On cooling, the mixture was poured onto crushed ice and basified with aqueous sodium acetate (50%, 20 ml). The organic phase was separated and the aqueous layer was extracted with ether. The combined organic extracts were washed with aqueous sodium hydrogen carbonate, dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on alumina (Brockmann grade 1) with ether - methanol (0-1% ) gradient elution gave the title compound (D29) as a beige solid (0.18 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 h
  2. temperatureOn cooling
  3. additionthe mixture was poured
  4. customonto crushed ice
  5. customThe organic phase was separated
  6. extractionthe aqueous layer was extracted with ether
  7. washThe combined organic extracts were washed with aqueous sodium hydrogen carbonate
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo
  10. customto give an oil
  11. washChromatography on alumina (Brockmann grade 1) with ether - methanol (0-1% ) gradient elution

Sources & evidence

ORD record
ord-c8b0bf3191b74e8d902ca2c92d291d7e
Source dataset
uspto-grants-1996_06
Patent number
US05523299

Reaction notes

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