Hydrochloric Acid → HCID 9933927, compound

HRID 1106877Notes

Reaction equation

HRID 1106877 reaction equation
C([NH:4][C:5]1[CH:27]=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[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)C.[OH-].[Na+].[ClH:35]>>[ClH:35].[NH2:4][C:5]1[CH:27]=[C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])[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]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18789918HCID 18789918, compound

Product 1

HCID 9933927HCID 9933927, compound

Procedure

1-(2-Acetamido-4-methanesulfonamidophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (1 g, 2.2 mmol) was heated in 3N HCl (10 ml) at the reflux temperature for 3 h. Thereafter, the reaction mixture was neutralized to a pH of 6-7 with a solution of 10% sodium hydroxide, followed by extraction with ethyl acetate; the organic extract was then dried with magnesium sulfate and the solvent was evaporated. The residue was subjected to column chromatography on silica gel using, as an eluent, chloroform containing methanol (5%-10%) to yield the titled compound 1-(2-amino-4-methanesulfonamidophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (0.79 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionthe organic extract
  3. dry with materialwas then dried with magnesium sulfate
  4. customthe solvent was evaporated
  5. additionchloroform containing methanol (5%-10%)

Sources & evidence

ORD record
ord-8e4db77294f043cabf9c6d0e89f91d7e
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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