Hydrochloric Acid → Hydrochloric Acid

HRID 1776470Notes

Reaction equation

HRID 1776470 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8](C)[C:9](=O)OC(C)(C)C)=[CH:5][C:4]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].[ClH:24].O1CCOCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][CH3:9])=[CH:5][C:4]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].[ClH:24]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 86679426HCID 86679426, compound

Product 2

HCID 313Hydrochloric AcidYield 100%HCID 86679427HCID 86679427, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-methoxy-3-(methylsulfonamido)benzyl(methyl)carbamate (60.4 mg, 0.175 mmol) was dissolved in DCM (5 ml), HCl 4M in dioxane (250 μl, 1.000 mmol) was added, and the reaction was stirred at RT overnight. Additional HCl 4M in dioxane (500 μl, 2.00 mmol) was added over 30 hours with stirring at the same temperature. The solvent was evaporated under vacuum, and the solid so obtained was triturated in DCM and filtered to give N-(2-methoxy-5-((methylamino)methyl)-phenyl)methanesulfonamide as hydrochloride (42.8 mg, 0.175 mmol, 100% yield, MS/ESI+ 245.3 [MH]+) that was used in the next step without further purification.

Workup

  1. stirringwith stirring at the same temperature
  2. customThe solvent was evaporated under vacuum
  3. customthe solid so obtained
  4. customwas triturated in DCM
  5. filtrationfiltered

Sources & evidence

ORD record
ord-eb7787c22e334d04a0cae19088af7fd9
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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