Thionyl Chloride → 3,5-Dichloro-4-(chloromethyl)-2-pyridinamine

HRID 1959587Notes

Reaction equation

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

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 18511693(2-Amino-3,5-dichloro-pyridin-4-yl)-methanol

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

Product 1

HCID 187528833,5-Dichloro-4-(chloromethyl)-2-pyridinamine

Procedure

(2-Amino-3,5-dichloro-pyridin-4-yl)-methanol (7 mg, 0.036 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): 211.0 [M+H+].

Sources & evidence

ORD record: ord-8882ff6dfb5947f094121c5ea4079373
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410134B2

Reaction notes

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