Thionyl Chloride → HCID 86650042, compound

HRID 1892535Notes

Reaction equation

HRID 1892535 reaction equation
O[CH2:2][C:3]1[S:7][C:6]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][CH2:2][C:3]1[S:7][C:6]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86227318HCID 86227318, compound

Product 1

HCID 86650042HCID 86650042, compoundYield 118.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a water bath at about 20° C., to a suspension of N-(4-{2-[5-(hydroxymethyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (500.0 mg, 1.771 mmol) in anhydrous chloroform (2.5 ml) was added dropwise thionyl chloride (0.77 ml, 10.6 mmol). After stirring at room temperature for 1 hr, the reaction mixture was concentrated under reduced pressure. Anhydrous chloroform (5 ml) was added to the residue and the mixture was concentrated again under reduced pressure. This operation was repeated 3 times to remove thionyl chloride azeotropically. The residue was dried under reduced pressure to give N-(4-{2-[5-(chloromethyl)thiophen-2-yl]ethyl}-1,3-thiazol-2-yl)acetamide (633.2 mg) as a pale-brown solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionAnhydrous chloroform (5 ml) was added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. customto remove thionyl chloride azeotropically
  5. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-52b459b498fc4117a3123f087dc5e625
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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