Thionyl Chloride → (6-Chloro(3-pyridyl)methyl] (2-chloroethylamino}ethanenitrile

HRID 549223Notes

Reaction equation

HRID 549223 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:12][CH2:13][CH2:14]O)[C:10]#[N:11])=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:12][CH2:13][CH2:14][Cl:18])[C:10]#[N:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 86624867(6-Chloro(3-pyridyl)methyl](2-hydroxyethylamino}ethanenitrile

Product 1

HCID 86624866(6-Chloro(3-pyridyl)methyl] (2-chloroethylamino}ethanenitrile

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent

Procedure

This compound was prepared in a manner analogous to that set forth in Step C of Example 1, using 5.7 grams (0.0255 mole) of 2-{[(6-chloro(3-pyridyl)methyl](2-hydroxyethylamino}ethanenitrile 3.2 grams (0.0268 mole) of thionyl chloride and one drop (catalyst) of pyridine in 50 mL of chloroform. The yield of the subject compound was 6.0 grams. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that set forth in Step C of Example 1

Sources & evidence

ORD record
ord-58378f85ee644cb2850e5714cffc67a6
Source dataset
uspto-grants-2011_05
Patent number
US07943642B2

Reaction notes

Loading…