Thionyl Chloride → HCID 21190267, compound

HRID 619424Notes

Reaction equation

HRID 619424 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[N:10]2[CH:17]=1)[CH3:6]>C(Cl)Cl>[ClH:3].[CH2:5]([C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Cl:3])[N:10]2[CH:17]=1)[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21190273HCID 21190273, compound

Product 1

HCID 21190267HCID 21190267, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture solution consisting of 8.8 ml (120.0 mmol) of thionyl chloride and 10 ml of methylene chloride was added, 4.23 g (24.0 mmol) of 2-ethyl-5-hydroxymethylimidazo[1,2-a]pyridine with small portions. The reaction mixture was stirred for one hour at room temperature. Then, the solvent and excess volume of thionyl chloride were distilled off under reduced pressure. To the residual white solid was added 30 ml of toluene. The mixture was stirred well, and the solvent was distilled off under reduced pressure. This process repeated twice to give 5.44 g of a crude product (99.0%, white solid), which was used for the subsequent reaction without purification.

Workup

  1. additionwas added
  2. distillationThen, the solvent and excess volume of thionyl chloride were distilled off under reduced pressure
  3. additionTo the residual white solid was added 30 ml of toluene
  4. stirringThe mixture was stirred well
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-02e5d386dc684d8ab2594f6e204eb5d2
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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