1,2-Dichloroethane → HCID 20190402, compound

HRID 1788764Notes

Reaction equation

HRID 1788764 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[C:9]([C:16]([OH:18])=O)[CH:8]=2)[CH:2]=1.CN(C)C=O.[Cl:24]CCCl>S(Cl)(Cl)=O>[ClH:24].[Cl:24][C:16]([C:9]1[CH:8]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14]2)=[O:18]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 21255107HCID 21255107, compound

Product 1

HCID 20190402HCID 20190402, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylic acid (13.3 g) in a mixture of thionyl chloride (19.2 cc), dimethylformamide (0.05 cc) and 1,2-dichloroethane (160 cc) is heated to a temperature of about 70° C. The suspension obtained is kept at a temperature of about 70° C. for 3 hours. The reaction mixture is cooled to a temperature of about 20° C. and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. The residue is suspended in cyclohexane (300 cc) and the solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C. The same operation is repeated twice. 1-Chloroformyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine hydrochloride (16.3 g) is thus obtained in the form of light green crystals melting at 205° C.

Workup

  1. customThe suspension obtained
  2. temperatureThe reaction mixture is cooled to a temperature of about 20° C.
  3. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C
  4. customthe solvent is evaporated off under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 60° C

Sources & evidence

ORD record
ord-98c4e0936fd54c8bbb7ca27429d6edc9
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

Loading…