Oxalyl chloride → HCID 70922242, compound

HRID 524970Notes

Reaction equation

HRID 524970 reaction equation
[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][C:5]=2[C:9]([OH:11])=O)[CH2:3][CH2:2]1.[C:12](Cl)(=O)[C:13](Cl)=O>ClCCl.CN(C)C=O>[CH:1]1([C:4]2[CH:8]=[CH:7][NH:6][C:5]=2[C:9]([NH:6][C:5]2[CH:4]=[CH:1][CH:2]=[CH:3][C:12]=2[CH3:13])=[O:11])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 793254551369142-11-9

Product 1

HCID 70922242HCID 70922242, compoundYield 186.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the 3-cyclopropyl-1H-pyrrole-2-carboxylic acid (50 mg, 0,33 mmol) in dry dichloromethane (0.4 mL) was added a solution of oxalyl chloride (0.04 mL, 0,37 mmol) in 0.3 mL of dichloromethane atroom temperatureand 3 drops of N,N-dimethylformamide. After 1.5 h at this temperature, the mixture was concentrated under vacuum and the residue was redissolved in dichloromethane (1 mL). To this solution was added a solution of o-toluidine in dichloromethane (0,2 mL) and the mixture was stirred at room temperature overnight. The reaction was worked-up diluting with dichloromethane and washing with sodium bicarbonate (2×) and brine. The organic phase was dried and concentrated to give 74 mg of the title compound (88% yield).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. dissolutionthe residue was redissolved in dichloromethane (1 mL)
  3. additionTo this solution was added a solution of o-toluidine in dichloromethane (0,2 mL)
  4. additionThe reaction was worked-up diluting with dichloromethane
  5. washwashing with sodium bicarbonate (2×) and brine
  6. customThe organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1e96c019287c400282873e82871fa601
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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