Acetic Acid → HCID 21930357, compound

HRID 1243761Notes

Reaction equation

HRID 1243761 reaction equation
[BrH:1].C(O)(=O)C.[CH2:6]([S:8][C:9]1[C:18]([O:19]C)=[CH:17][CH:16]=[CH:15][C:10]=1[CH2:11][N:12]([CH3:14])[CH3:13])[CH3:7]>C(OCC)C>[BrH:1].[CH3:14][N:12]([CH2:11][C:10]1[C:9]([S:8][CH2:6][CH3:7])=[C:18]([OH:19])[CH:17]=[CH:16][CH:15]=1)[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 21930460HCID 21930460, compound

Product 1

HCID 21930357HCID 21930357, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
100 °C

Procedure

30% Hydrogen bromide in acetic acid (3.6 mL, 18.05 mmol) was added to (2-ethylsulfanyl-3-methoxybenzyl)-dimethylamine (800 mg, 3.55 mmol) and the reaction mixture was heated with stirring at 100° C. After 17 h, the reaction was complete by LC/MS analysis and was then allowed to cool to room temperature. Diethyl ether (1.00 mL) was added with stirring and after 20 min the orange diethyl ether solution was decanted off. This procedure was repeated until a tan solid precipitated. 3-Dimethylaminomethyl-2-ethylsulfanyl-phenol hydrobromide (770 mg, 100%) was filtered off as a tan solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto cool to room temperature
  3. customwas decanted off
  4. customprecipitated
  5. filtration3-Dimethylaminomethyl-2-ethylsulfanyl-phenol hydrobromide (770 mg, 100%) was filtered off as a tan solid

Sources & evidence

ORD record
ord-981accf8fd9444b69d08c0b49b1707a5
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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