Acetic Acid → 3-Dimethylaminomethyl-2-methylsulfanyl-phenol hydrobromide

HRID 1243756Notes

Reaction equation

HRID 1243756 reaction equation
[BrH:1].C(O)(=O)C.[CH3:6][S:7][C:8]1[C:17]([O:18]C)=[CH:16][CH:15]=[CH:14][C:9]=1[CH2:10][N:11]([CH3:13])[CH3:12]>C(OCC)C>[BrH:1].[CH3:13][N:11]([CH2:10][C:9]1[C:8]([S:7][CH3:6])=[C:17]([OH:18])[CH:16]=[CH:15][CH:14]=1)[CH3:12]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 21930394(2-Methylsulfanyl-3-methoxybenzyl)-dimethylamine

Product 1

HCID 219303513-Dimethylaminomethyl-2-methylsulfanyl-phenol hydrobromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

30% Hydrogen bromide in acetic acid (7 mL, 34 mmol) was added to (2-methylsulfanyl-3-methoxybenzyl)-dimethylamine (1.44 g, 6.8 mmol) and 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 (100 mL) was added with stirring. After 20 min, the orange diethyl ether solution was decanted off. This was repeated until a tan solid precipitated. 3-Dimethylaminomethyl-2-methylsulfanyl-phenol hydrobromide (1.74 g, 90%) was filtered off as a brown solid.

Workup

  1. temperatureheated
  2. temperatureto cool to room temperature
  3. stirringwith stirring
  4. waitAfter 20 min
  5. customthe orange diethyl ether solution was decanted off
  6. customprecipitated
  7. filtration3-Dimethylaminomethyl-2-methylsulfanyl-phenol hydrobromide (1.74 g, 90%) was filtered off as a brown solid

Sources & evidence

ORD record
ord-4ae764e5824e4c6faf7b9b7b949f8003
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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