Thionyl Chloride → 2-(5-Chloro-4-chloromethyl-pyridin-3-ylsulfanyl)-N-isopropyl-N-methyl-acetamide

HRID 1959573Notes

Reaction equation

HRID 1959573 reaction equation
[Cl:1][C:2]1[C:3]([CH2:17]O)=[C:4]([S:8][CH2:9][C:10]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[O:11])[CH:5]=[N:6][CH:7]=1.O=S(Cl)[Cl:21].ClC1C=NC=C(Cl)C=1CCl>>[Cl:1][C:2]1[C:3]([CH2:17][Cl:21])=[C:4]([S:8][CH2:9][C:10]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 226268533,5-Dichloro-4-(chloromethyl)pyridineHCID 670771792-(5-Chloro-4-hydroxymethyl-pyridin-3-ylsulfanyl)-N-isopropyl-N-methyl-acetamide

Product 1

HCID 670775232-(5-Chloro-4-chloromethyl-pyridin-3-ylsulfanyl)-N-isopropyl-N-methyl-acetamide

Procedure

2-(5-Chloro-4-hydroxymethyl-pyridin-3-ylsulfanyl)-N-isopropyl-N-methyl-acetamide (7.5 mg, 0.026 mmol) was chlorinated with SOCl2 according to the synthesis of 3,5-dichloro-4-chloromethyl-pyridine to give the title compound. MS (m/z): 307.0 [M+H+].

Sources & evidence

ORD record
ord-fe13fc3fbc54459bb3fb2d5c654a9beb
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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