Hydrochloric Acid → HCID 14257566, compound

HRID 2291951Notes

Reaction equation

HRID 2291951 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([N:13]([CH2:27][CH:28]([OH:30])[CH3:29])[S:14]([C:17]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:16])=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].Cl>O.C(N(CC)CC)C.ClCCl.CS(C)=O>[CH2:27]([N:13]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[S:14]([C:17]1[C:18]2[CH:19]=[CH:20][N:21]=[CH:22][C:23]=2[CH:24]=[CH:25][CH:26]=1)(=[O:15])=[O:16])[C:28]([CH3:29])=[O:30]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 14257565HCID 14257565, compound

Product 1

HCID 14257566HCID 14257566, compoundYield 86.5%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Conditions

Temperature
-55 °C

Procedure

To 60 ml of a dried dichloromethane solution containing 2.4 ml of oxalyl chloride was added dropwise at -50° C. 12 ml of a dichloromethane solution containing 4.08 ml of dimethylsulfoxide. To the mixture was added dropwise over a period of 20 minutes, while maintaining the temperature at -55° C., 4 ml of a dried dichloromethane solution containing 8.34 g of N-hexyl-N-(2-hydroxypropyl)-5-isoquinolinesulfonamide, followed by stirring at -50° C. to -60° C. for 15 minutes. To the resulting mixture was added 16.8 ml of triethylamine, and the temperature of the mixture was elevated to 15° to 20° C. over a period of 1.5 hours. To the resulting reaction mixture was added 100 ml of water, and the pH was adjusted to 5 with 1N hydrochloric acid solution. The dichloromethane layer was washed with 50 ml of a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. Then, the dichloromethane was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 200 g; solvent: a 2% methanol solution in chloroform) to obtain 7.17 g of N-acetonyl-N-hexyl-5-isoquinolinesulfonamide.

Workup

  1. additionwas added dropwise at -50° C
  2. additionTo the mixture was added dropwise over a period of 20 minutes
  3. waitthe temperature of the mixture was elevated to 15° to 20° C. over a period of 1.5 hours
  4. customTo the resulting reaction mixture
  5. washThe dichloromethane layer was washed with 50 ml of a saturated aqueous sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThen, the dichloromethane was removed under reduced pressure
  8. customto obtain a residue
  9. customThe residue thus obtained
  10. customwas subjected to purification by silica gel column chromatography (Wacogel C-200, 200 g

Sources & evidence

ORD record
ord-0dc12ac40ae045a6b2c58098d88ffa94
Source dataset
uspto-grants-1989_01
Patent number
US04798897

Reaction notes

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