Dimethylformamide → HCID 86633781, compound

HRID 1672364Notes

Reaction equation

HRID 1672364 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([S:19]([OH:22])(=O)=[O:20])[C:12]3[CH:13]=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=2)=[CH:5][CH:4]=1.CN(C=O)C.C(Cl)(=O)C([Cl:31])=O>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([S:19]([Cl:31])(=[O:22])=[O:20])[C:12]3[CH:13]=[CH:14][N:15]=[CH:16][C:17]=3[CH:18]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86633782HCID 86633782, compound

Product 1

HCID 86633781HCID 86633781, compoundYield 115.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
62.5 °C

Procedure

To a slurry of 7-(4-methoxy-phenyl)-isoquinoline-5-sulfonic acid (12.13 g, 38.5 mmol) in 1,2-dichloroethane (200 mL) and DMF (2.99 mL, 38.5 mmol) add oxalyl chloride (26.8 mL, 308 mmol) dropwise. Mechanically stir the slurry under nitrogen atmosphere while heating at 60-65° C. for 4 hr. Cool the slurry to −10° C. Wait for 30 min then filter. Wash the yellow solid with 20% ether/dichloromethane and dry under a nitrogen atmosphere affording the title compound (14.8 g) as a yellow powder.

Workup

  1. temperatureCool the slurry to −10° C
  2. filtrationthen filter
  3. washWash the yellow solid with 20% ether/dichloromethane
  4. customdry under a nitrogen atmosphere

Sources & evidence

ORD record
ord-4ca403d36c874b9698c4e07e1ad53c26
Source dataset
uspto-grants-2011_08
Patent number
US07998977B2

Reaction notes

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