Thionyl Chloride → Dimethyl-carbamic acid 6-amino-5-chloro-4-chloromethyl-pyridin-3-ylmethyl ester

HRID 1959588Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C:10](=[O:14])[N:11]([CH3:13])[CH3:12])=[C:4]([CH2:15]O)[C:3]=1[Cl:17].O=S(Cl)[Cl:20].ClC1C=NC=C(Cl)C=1CCl>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C:10](=[O:14])[N:11]([CH3:13])[CH3:12])=[C:4]([CH2:15][Cl:20])[C:3]=1[Cl:17]

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 226268533,5-Dichloro-4-(chloromethyl)pyridine

HCID 67078166Dimethyl-carbamic acid 6-amino-5-chloro-4-hydroxymethyl-pyridin-3-ylmethyl ester

Product 1

HCID 67077397Dimethyl-carbamic acid 6-amino-5-chloro-4-chloromethyl-pyridin-3-ylmethyl ester

Procedure

Dimethyl-carbamic acid 6-amino-5-chloro-4-hydroxymethyl-pyridin-3-ylmethyl ester (18.5 mg, 0.071 mmol) was chlorinated with SOCl2 according to the synthesis of 3,5-dichloro-4-chloromethyl-pyridine. The resulting title compound was used for the next reaction without purification. MS (m/z): 278.0 [M+H+].

Sources & evidence

ORD record: ord-b7e9cd25355c4625b7f4be63c9b2c79c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410134B2

Reaction notes

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