Thionyl Chloride → HCID 178491094, compound

HRID 1875565Notes

Reaction equation

HRID 1875565 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:9]O)[N:3]=[CH:2]1.S(Cl)([Cl:22])=O>O1CCOCC1>[NH:1]1[CH:5]=[C:4]([CH2:6][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:9][Cl:22])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178491110HCID 178491110, compound

Product 1

HCID 178491094HCID 178491094, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(((1H-imidazol-4-yl)methyl)(4-methoxybenzyl)amino)ethanol (Step B, 14.5 g, 55.55 mmol) in anhydrous dioxane (100 mL) was added thionyl chloride (16.5 mL, 222.2 mmol) over a 10 minute period. The reaction mixture was heated at 60° C. for 3 hours, cooled to room temperature and partitioned under reduced pressure. The contents of the flask were azeotroped with dioxane (2×100 mL) and toluene (2×100 mL). The white solid c that separates out is filtered and used as such for the subsequent step without further purification (19.0 g).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned under reduced pressure
  3. customThe contents of the flask were azeotroped with dioxane (2×100 mL) and toluene (2×100 mL)
  4. filtrationThe white solid c that separates out is filtered
  5. customwithout further purification (19.0 g)

Sources & evidence

ORD record
ord-36a61370ee9d499fae56a1d3bbece901
Source dataset
uspto-grants-2012_11
Patent number
US08309571B2

Reaction notes

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