Methanesulfonyl chloride → HCID 18789928, compound

HRID 1106876Notes

Reaction equation

HRID 1106876 reaction equation
[C:1]([NH:4][C:5]1[CH:27]=[C:26]([NH2:28])[CH:25]=[CH:24][C:6]=1[O:7][CH2:8][CH2:9][N:10]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[CH3:11])(=[O:3])[CH3:2].[CH3:29][S:30]([Cl:33])(=[O:32])=[O:31]>N1C=CC=CC=1>[ClH:33].[C:1]([NH:4][C:5]1[CH:27]=[C:26]([NH:28][S:30]([CH3:29])(=[O:32])=[O:31])[CH:25]=[CH:24][C:6]=1[O:7][CH2:8][CH2:9][N:10]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[CH3:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18789879HCID 18789879, compound

Product 1

HCID 18789928HCID 18789928, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A portion (510 mg, 1.32 mmol) of the 1-(2-acetamido-4-aminophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (4) above was dissolved in pyridine (5 ml) and, thereafter, the solution was cooled to 0° C. and methanesulfonyl chloride (0.21 ml, 2.63 mmol) was added, followed by stirring at room temperature for 2 h. Thereafter, the solvent was evaporated from the reaction mixture and the resulting residue was diluted with an aqueous solution of sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried with sodium sulfate and the solvent was evaporated, with the resulting residue being purified by being subjected to column chromatography on silica gel using, as an eluent, chloroform containing methanol (6%). The resulting product was dissolved in methanol (10 ml) and the HCl as generated by adding conc. sulfuric acid to ammonium chloride was passed through the resulting solution. Thereafter, the solvent was evaporated for drying to yield the titled compound 1-(2-acetamido-4-methanesulfonamidophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (420 mg) as a foamy substance of ivory color.

Workup

  1. customThereafter, the solvent was evaporated from the reaction mixture
  2. additionthe resulting residue was diluted with an aqueous solution of sodium bicarbonate
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. customthe solvent was evaporated, with the resulting residue
  6. custombeing purified
  7. additionchloroform containing methanol (6%)
  8. dissolutionThe resulting product was dissolved in methanol (10 ml)
  9. additionby adding conc. sulfuric acid to ammonium chloride
  10. customThereafter, the solvent was evaporated
  11. customfor drying

Sources & evidence

ORD record
ord-7e1726479b084de99c659fbe9140e2d7
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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