Dimethylformamide → HCID 136411693, compound

HRID 1828886Notes

Reaction equation

HRID 1828886 reaction equation
[C:1]([C:4]1[C:5]([CH3:21])=[C:6]([CH:10]=[C:11]2[C:15](=[O:16])[NH:14][N:13]=[C:12]2[O:17][CH:18]([CH3:20])[CH3:19])[NH:7][C:8]=1[CH3:9])([OH:3])=[O:2].CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH3:33][N:34]([CH2:36][CH2:37]O)[CH3:35]>ClCCl>[CH3:33][N:34]([CH3:35])[CH2:36][CH2:37][O:2][C:1]([C:4]1[C:5]([CH3:21])=[C:6]([CH:10]=[C:11]2[C:15](=[O:16])[NH:14][N:13]=[C:12]2[O:17][CH:18]([CH3:19])[CH3:20])[NH:7][C:8]=1[CH3:9])=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 79022-(Dimethylamino)ethanolHCID 65578Oxalyl chlorideHCID 136411694HCID 136411694, compound

Product 1

HCID 136411693HCID 136411693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-[(4-carboxy-3,5-dimethylpyrrol-2-yl)methylene]-3-isopropoxy-2-pyrazolin-5-one (200 mg, 0.68 mmol) in dichloromethane (20 ml) and a drop of DMF, was treated with oxalyldichloride (0.2 ml). The stirring was continued for 24 h and a solution of dimethylaminoethanol (0.6 g, 6.7 mmol) in dichloromethane (5 ml) was added. The stirring was continued for 24 h. The solvent was evaporated to dryness, the solid residue was treated with NaHCO3 (5%) and extracted with dichloromethane. The solid obtained after elimination of the solvent was recrystallized from n-heptane.

Workup

  1. waitThe stirring was continued for 24 h
  2. customThe solvent was evaporated to dryness
  3. additionthe solid residue was treated with NaHCO3 (5%)
  4. extractionextracted with dichloromethane
  5. customThe solid obtained after elimination of the solvent
  6. customwas recrystallized from n-heptane

Sources & evidence

ORD record
ord-50c79ad8e3e144349af26aba86ed932a
Source dataset
uspto-grants-2006_06
Patent number
US07060822B1

Reaction notes

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