Cysteamine → 2-(3,4-Dimethoxy-2-pyridylmethylthio)ethylamine

HRID 237068Notes

Reaction equation

O[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][N:4]=1.S(Cl)(Cl)=O.[NH2:17][CH2:18][CH2:19][SH:20]>>[CH3:10][O:9][C:8]1[C:3]([CH2:2][S:20][CH2:19][CH2:18][NH2:17])=[N:4][CH:5]=[CH:6][C:7]=1[O:11][CH3:12]

Participants

Reactant 3

HCID 6058Cysteamine

HCID 24386Thionyl Chloride

HCID 107258093,4-Dimethoxy-2-pyridinemethanol

Product 1

HCID 202792822-(3,4-Dimethoxy-2-pyridylmethylthio)ethylamine

Procedure

3-Fluoro-2-methyl-4-nitropyridine N-oxide is treated with an excess of sodium methoxide and the product is heated in acetic anhydride and deacetylated to give 2-hydroxymethyl-3,4-dimethoxypyridine. 2-Hydroxymethyl-3,4-dimethoxypryidine is treated with thionyl chloride and the product is treated with cysteamine to give 2-(3,4-dimethoxy-2-pyridylmethylthio)ethylamine.

Sources & evidence

ORD record: ord-c9e51e5977ba400a8cdd1adb52d6fc7a
Source dataset: uspto-grants-1979_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04159329

Reaction notes

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