Thionyl Chloride → HCID 67467008, compound

HRID 1406316Notes

Reaction equation

HRID 1406316 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7]O)=[N:4][C:3]=1[CH2:9][CH3:10].S(Cl)([Cl:13])=O>C1COCC1>[Br:1][C:2]1[S:6][C:5]([CH2:7][Cl:13])=[N:4][C:3]=1[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67462280HCID 67462280, compound

Product 1

HCID 67467008HCID 67467008, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-bromo-4-ethylthiazol-2-yl)methanol (313 mg 1.41 mmol) in THF (15 ml) under nitrogen at room temperature was added thionyl chloride (0.206 ml 2.82 mmol) and stirred overnight. LCMS indicated the completion of the reaction. A saturated ice cold aqueous NaHCO3 solution was added to the reaction solution with gas evolution. The mixture was extracted with EtOAc (4×20 ml), dried over sodium sulfate and concentrated to give a brown oil 301 mg, 89% which was used for the next step without further purification.

Workup

  1. customthe completion of the reaction
  2. extractionThe mixture was extracted with EtOAc (4×20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9d3e2c4307042a7b2604437d074a682
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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