Thionyl Chloride → HCID 20455444, compound

HRID 1263322Notes

Reaction equation

HRID 1263322 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:2]=1.S(Cl)([Cl:18])=O>CN(C)C=O>[ClH:18].[Cl:18][C:13]([C:7]1([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:12][CH2:11][CH2:10][CH2:9][S:8]1)=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10104998HCID 10104998, compound

Product 1

HCID 20455444HCID 20455444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

The 2-(pyrid-3-yl)-tetrahydrothiopyran-2-carboxylic acid thus obtained (16.4 g) is added in small portions, in the course of 30 minutes, to thionyl chloride (25 cc) to which dimethylformamide (0.05 cc) has been added. The reaction mixture is then stirred at the boil for 2 hours 30 minutes, cooled to a temperature of about 20° C. and then concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 70° C. This gives crude 2-chloroformyl-2-(pyrid-3-yl)-tetrahydrothiopyran hydrochloride (26 g) in the form of an orange oil, which is used immediately without further purification.

Workup

  1. additionhas been added
  2. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 70° C

Sources & evidence

ORD record
ord-bd857bba5bb84e0c98d46a0065958095
Source dataset
uspto-grants-1984_06
Patent number
US04456758

Reaction notes

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